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  • 1.
    Ahlgren, Joakim
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för fysikalisk och analytisk kemi, Analytisk kemi.
    Reitzel, Kasper
    Tranvik, Lars
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Biologiska sektionen, Institutionen för ekologi och evolution, Limnologi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Rydin, Emil
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Biologiska sektionen, Institutionen för ekologi och evolution, Limnologi.
    Degradation of organic phosphorus compounds in anoxic Baltic Sea sediments: A P-31 nuclear magnetic resonance study2006Inngår i: Limnology and Oceanography, ISSN 0024-3590, E-ISSN 1939-5590, Vol. 51, nr 5, s. 2341-2348Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The composition and abundance of phosphorus extracted by NaOH-ethylenediaminetetraacetic acid from anoxic Northwest Baltic Sea sediment was characterized and quantified using solution P-31 nuclear magnetic resonance. Extracts from sediment depths down to 55 cm, representing 85 yr of deposition, contained 18.5 g m(-2) orthophosphate. Orthophosphate monoesters, teichoic acid P, microbial P lipids, DNA P, and pyrophosphate corresponded to 6.7, 0.3, 1.1, 3.0, and 0.03 g P m(-2), respectively. The degradability of these compound groups was estimated by their decline in concentration with sediment depth. Pyrophosphate had the shortest half-life (3 yr), followed by microbial P lipids with a half-life of 5 yr, DNA P (8 yr), and orthophosphate monoesters (16 yr). No decline in concentration with sediment depth was observed for orthophosphate or teichoic acid P.

  • 2. Aili, Daniel
    et al.
    Enander, Karin
    Baltzer, Lars
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Liedberg, Bo
    Assembly of polypeptide-functionalized gold nanoparticles through a heteroassociation- and folding-dependent bridging2008Inngår i: Nano letters (Print), ISSN 1530-6984, E-ISSN 1530-6992, Vol. 8, nr 8, s. 2473-2478Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Gold nanoparticles were functionalized with a synthetic polypeptide, de novo-designed to associate with a charge complementary linker polypeptide in a folding-dependent manner. A heterotrimeric complex that folds into two disulphide-linked four-helix bundles is formed when the linker polypeptide associates with two of the immobilized peptides. The heterotrimer forms in between separate particles and induces a rapid and extensive aggregation with a well-defined interpartide spacing. The aggregated particles are redispersed when the disulphide bridge in the linker polypeptide is reduced.

  • 3.
    Andersson, Claes-Henrik
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Berggren, Gustav
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för fotokemi och molekylärvetenskap.
    Ott, Sascha
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för fotokemi och molekylärvetenskap, Molekylär biomimetik.
    Grennberg, Helena
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Synthesis and IR Spectroelectrochemical Studies of a [60]Fulleropyrrolidine-(tricarbonyl)chromium Complex: Probing C-60 Redox States by IR Spectroscopy2011Inngår i: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, nr 11, s. 1744-1749Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The synthesis of a new fulleropyrrolidine-(tricarbonyl)chromium complex: 1-methyl-2-(4-methoxyphenyl)-3,4-[60]fulleropyrrolidine-(tricarbonyl)chromium is described together with its characterization by IR, NMR and cyclic voltammetry. IR spectro-electrochemistry has been used to probe the redox level of the fullerene derivative via the relative position of the vibrational bands of the CO ligands, which are sensitive to the electronic state of the complex. Other strategies to incorporate a tricarbonylchromium moiety to fullerene C60 are also briefly discussed and evaluated.

  • 4.
    Baltzer, Lars
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Crossing borders to bind proteins-a new concept in protein recognition based on the conjugation of small organic molecules or short peptides to polypeptides from a designed set2011Inngår i: Analytical and Bioanalytical Chemistry, ISSN 1618-2642, E-ISSN 1618-2650, Vol. 400, nr 6, s. 1653-1664Artikkel, forskningsoversikt (Fagfellevurdert)
    Abstract [en]

    A new concept for protein recognition and binding is highlighted. The conjugation of small organic molecules or short peptides to polypeptides from a designed set provides binder molecules that bind proteins with high affinities, and with selectivities that are equal to those of antibodies. The small organic molecules or peptides need to bind the protein targets but only with modest affinities and selectivities, because conjugation to the polypeptides results in molecules with dramatically improved binder performance. The polypeptides are selected from a set of only sixteen sequences designed to bind, in principle, any protein. The small number of polypeptides used to prepare high-affinity binders contrasts sharply with the huge libraries used in binder technologies based on selection or immunization. Also, unlike antibodies and engineered proteins, the polypeptides have unordered three-dimensional structures and adapt to the proteins to which they bind. Binder molecules for the C-reactive protein, human carbonic anhydrase II, acetylcholine esterase, thymidine kinase 1, phosphorylated proteins, the D-dimer, and a number of antibodies are used as examples to demonstrate that affinities are achieved that are higher than those of the small molecules or peptides by as much as four orders of magnitude. Evaluation by pull-down experiments and ELISA-based tests in human serum show selectivities to be equal to those of antibodies. Small organic molecules and peptides are readily available from pools of endogenous ligands, enzyme substrates, inhibitors or products, from screened small molecule libraries, from phage display, and from mRNA display. The technology is an alternative to established binder concepts for applications in drug development, diagnostics, medical imaging, and protein separation.

  • 5.
    Blom, Tobias
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Tillämpad materialvetenskap.
    Jafri, Hassan
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Tillämpad materialvetenskap.
    Di Cristo, Valentina
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Tillämpad materialvetenskap.
    Carva, Karel
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Fysiska sektionen, Institutionen för fysik och astronomi, Materialteori.
    Possnert, Göran
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Fysiska sektionen, Institutionen för fysik och astronomi, Högenergifysik.
    Sanyal, Biplab
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Fysiska sektionen, Institutionen för fysik och astronomi, Materialteori.
    Grennberg, Helena
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi. Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Jansson, Ulf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för materialkemi, Oorganisk kemi.
    Eriksson, Olle
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Fysiska sektionen, Institutionen för fysik och astronomi, Materialteori.
    Leifer, Klaus
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Tillämpad materialvetenskap.
    Conduction properties of graphene as a function of ion irradiation and acid treatment2011Inngår i: Graphene 2011 - 11th to 14th April 2011. Bilbao, Spain., 2011Konferansepaper (Fagfellevurdert)
  • 6.
    Bohl Kullberg, Erika
    et al.
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Medicinska fakulteten, Institutionen för onkologi, radiologi och klinisk immunologi, Enheten för biomedicinsk strålningsvetenskap.
    Bergstrand, Nill
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Fysikalisk-kemiska institutionen.
    Carlsson, Jörgen
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Medicinska fakulteten, Institutionen för onkologi, radiologi och klinisk immunologi, Enheten för biomedicinsk strålningsvetenskap.
    Edwards, Katarina
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Fysikalisk-kemiska institutionen.
    Johnsson, Markus
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Fysikalisk-kemiska institutionen.
    Sjöberg, Stefan
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gedda, Lars
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Medicinska fakulteten, Institutionen för onkologi, radiologi och klinisk immunologi, Enheten för biomedicinsk strålningsvetenskap.
    Development of EGF-conjugated liposomes for targeted delivery of boronated DNA-binding agents2002Inngår i: Bioconjugate chemistry, ISSN 1043-1802, E-ISSN 1520-4812, Vol. 13, nr 4, s. 737-743Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Liposomes are of interest as drug delivery tools for therapy of cancer and infectious diseases. We investigated conjugation of epidermal growth factor, EGF, to liposomes using the micelle-transfer method. EGF was conjugated to the distal end of PEG−DSPE lipid molecules in a micellar solution and the EGF−PEG−DSPE lipids were then transferred to preformed liposomes, either empty or containing the DNA-binding compound, water soluble acridine, WSA. We found that the optimal transfer conditions were a 1-h incubation at 60 °C. The final conjugate, 125I-EGF−liposome−WSA, contained approximately 5 mol % PEG, 10−15 EGF molecules at the liposome surface, and 104 to 105 encapsulated WSA molecules could be loaded. The conjugate was shown to have EGF-receptor-specific cellular binding in cultured human glioma cells.

  • 7.
    Bäckvall, Jan-Erling
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Evidence for (π-allyl)palladium(II)(quinone) complexes in the palladium-catalyzed 1,4-diacetoxylation of conjugated dienes1988Inngår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 29, nr 18, s. 2243-2246Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Evidence for a coordination of p-benzoquinone to palladium in [4-acetoxy-η3-(1,2,3)-cyclohexenyl]-palladium(II) complexes was provided by changes of the 1H NMR chemical shift values of the π-allyl protons and a decrease of the spin-lattice relaxation time constant for the p-benzoquinone protons.

    The intermediate (π-allyl)palladium(benzoquinone) complexes previously postulated in palladium-catalyzed 1,4-oxidations of 1,3-dienes were detected by NMR spectroscopy.

  • 8.
    Bäckvall, Jan-Erling
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Palladium‑Hydroquinone Catalysed Electrochemical 1,4‑Oxidation of Conjugated Dienes1987Inngår i: Journal of the Chemical Society. Chemical communications, ISSN 0022-4936, Vol. 16, s. 1236-1238Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The mediator system palladium(II)–hydroquinone was shown to catalyse the anodic oxidation of cyclohexa-1,3-diene in acetic acid to produce selectively either trans- or cis-1,4-diacetoxycyclohex-2-ene (1) depending on the conditions.

  • 9.
    Bökman, Fredrik
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Bohman, Ove
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Pettersson, L. G. M.
    UNIV STOCKHOLM, DEPT THEORET PHYS, S-11346 STOCKHOLM, SWEDEN.
    Siegbahn, Hans O. G.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Fysiska sektionen.
    Electronic Structure of Catalytically Important Palladium Complexes Studied by Photoelectron Spectroscopy1992Inngår i: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 11, nr 5, s. 1784-1788Artikkel i tidsskrift (Fagfellevurdert)
  • 10.
    Church, Tamara L.
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
    Rasmussen, Torben
    Andersson, Pher G.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Enantioselectivity in the Iridium-Catalyzed Hydrogenation of Unfunctionalized Olefins2010Inngår i: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 29, nr 24, s. 6769-6781Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The iridium catalyzed asymmetric hydrogenation of largely unfunctionalized olefins has been studied by DFT calculations using a full experimentally tested combination of ligand and substrate All possible diastereomeric pathways were considered within four different hydrogenation mechanisms The effect of a solvent continuum was also considered and both the gas phase and solvent continuum calculations favored the same mechanism This mechanism passed through Ir-III and Ir-V intermediates and was consistent with the sense of stereoselection observed experimentally Comparing the calculations to those performed on a model system permitted an evaluation of the model system s utility in representing the full one A simple general method for predicting the sense of stereoselection in iridium-catalyzed olefin hydrogenation was developed and tested against published data

  • 11.
    Dinér, Peter
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Catalytic asymmetric chiral lithium amide-promoted epoxide rearrangement: a NMR spectroscopic and kinetic investigation2010Inngår i: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 21, nr 21-22, s. 2733-2739Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The lithium amide derived from the chiral diamine (1R,3S,4S)-3-(1-pyrrolidinyl)methyl-2-azabicyclo[2.2.1]heptane, has been reported to catalytically deprotonate cyclohexene oxide and other epoxides, yielding chiral allylic alcohols in excellent enantiomeric excess. In this work, 6Li, 1H and 13 C NMR spectroscopy have been used to study the aggregation of the chiral lithium amide in THF and the influence on the aggregation by the addition of additives, such as 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU). The activated complex under catalytic deprotonation of cyclohexene oxide, that is, with excess Li-DBU and free DBU, is built from one monomer of the chiral lithium amide, one molecule of epoxide and one additional molecule of DBU. The reaction order (0.97) obtained for the bulk base Li-DBU shows an inverse dependence on the concentration, suggesting a deaggregation of the initial mixed dimer to a monomer-based transition state containing a monomer of the lithium amide.

  • 12.
    Engdahl, Carin
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Eklund, Ulf
    UMEA UNIV, DEPT ORGAN CHEM, NMR RES GRP, S-90187 UMEA, SWEDEN .
    Long‑Range Deuterium Isotope Effects on 13C NMR Shifts of Intramolecularly Hydrogen‑Bonded 9‑Hydroxyphenalen‑1‑ones1991Inngår i: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 29, nr 1, s. 54-62Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The 1H and 13C NMR spectra of 9-hydroxyphenalenone (1) and 9-hydroxy-2-methylphenalenone (2) have been completely assigned. Primary and secondary deuterium isotope effects were determined in three solvents (chloroform, acetone and dimethyl sulphoxide), including the effect of temperature on the secondary isotope effects. Both negative and large long-range secondary isotope effects were found for both 1 and 2. The average secondary isotope effects for corresponding carbons follow the same sign and magnitude pattern in both compounds.

  • 13.
    Erdelyi, Mate
    et al.
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi. Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Rapid microwave-assisted solid phase peptide synthesis2002Inngår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 11, s. 1592-1596Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A microwave-assisted, rapid solid phase peptide synthesis procedure is presented. It has been applied to the coupling of sterically hindered Fmoc-protected amino acids yielding di- and tripeptides. Optimized conditions for a variety of coupling reagents are reported. Peptides were obtained rapidly (1.5-20 min) and without racemization.

  • 14.
    Erlandsson, Maria
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Imaging of Enzymes in the Steroid Biosynthetic Pathway: Synthesis of 18F-Labelled Tracers2009Doktoravhandling, med artikler (Annet vitenskapelig)
    Abstract [en]

    This thesis deals with the synthesis and development of 18F-labelled alkyl etomidate and vorozole analogues, and their use as positron emission tomography (PET) tracers for the imaging of the steroid enzymes 11β-hydroxylase and aromatase. Two synthetic 18F-labelling approaches to the etomidate and vorozole analogues were developed, and the analogues were evaluated in some biological assays.

    The two-step labelling method was used to synthesise many compounds for biological evaluation. In the first step, a 18F-labelled intermediate based on a ditosylate or a halogenated diethyl ether was synthesised and used directly in the next alkylation step. The decay-corrected (d.c.) radiochemical yield was higher compared to other known two-step labelling methods.

    Once an appropriate candidate has been chosen for clinical evaluation, a one-step labelling method will be more suitable. We therefore developed a method based on precursors that had leaving groups at the end of their alkyl chains, and used these directly in the 18F-labelling synthesis. The one-step 18F-labelling synthesis required less reaction time and produced higher specific radioactivity and d.c. radiochemical yield than our two-step synthesis. With microwave heating, the reaction time was reduced to seconds and the d.c. radiochemical yield was better than that obtained with conventional heating. The one-step synthesis simplified the technical handling by allowing the tracer syntheses to be automated on the TRACERLab FXFN.

    Delarbeid
    1. Synthesis of 11C-labelled metomidate analogues as adrenocortical imaging agents
    Åpne denne publikasjonen i ny fane eller vindu >>Synthesis of 11C-labelled metomidate analogues as adrenocortical imaging agents
    2008 (engelsk)Inngår i: J. Label Compd Radiopharm, nr 51, s. 273-276Artikkel i tidsskrift (Fagfellevurdert) Published
    HSV kategori
    Identifikatorer
    urn:nbn:se:uu:diva-16689 (URN)doi:10.1002/jlcr.1517 (DOI)
    Tilgjengelig fra: 2008-06-24 Laget: 2008-06-24 Sist oppdatert: 2011-01-11
    2. 18F-Labelled Metomidate Analogues as Adrenocortical Imaging Agents
    Åpne denne publikasjonen i ny fane eller vindu >>18F-Labelled Metomidate Analogues as Adrenocortical Imaging Agents
    2009 (engelsk)Inngår i: Nuclear Medicine and Biology, ISSN 0969-8051, E-ISSN 1872-9614, Vol. 36, nr 4, s. 435-445Artikkel i tidsskrift (Fagfellevurdert) Published
    Abstract [en]

    Introduction: Two- and one-step syntheses of 18F-labelled analogues of Metomidate, such as 2-[18F]fluoroethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate (1), 2-[18F]fluoroethyl 1-[(1R)-1-(4-chlorophenyl)ethyl]-1H-imidazole-5-carboxylate (2), 2-[18F]fluoroethyl 1-[(1R)-1-(4-bromophenyl)ethyl]-1H-imidazole-5-carboxylate (3), 3-[18F]fluoropropyl 1-[(1R)-1-(4-bromophenyl)ethyl]-1H-imidazole-5-carboxylate (4) and 3-[18F]fluoropropyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate (5) are presented.

    Methods: Analogues 1-5 were prepared by a two-step reaction sequence that started with the synthesis of either 2-[18F]fluoroethyl 4-methylbenzenesulfonate or 3-[18F]fluoropropyl 4-methylbenzenesulfonate. These were used as 18F-alkylating agents in the second step, in which they reacted with the ammonium salt of a 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylic acid. One-step-labelling syntheses of 1, 2 and 5 were also explored. Analogues 1-4 were biological validated by frozen-section autoradiography and organ distribution. Metabolite analysis was performed for 2 and 3.

    Results: The radiochemical yield of the two-step synthesis was in the range of 10-29%, and thatof the one-step synthesis was 25-37%. Using microwave irradiation in the one-step synthesis of 1 and 2 increased the radiochemical yield to 46 ± 3 and 79 ± 30%, respectively.

    Conclusion: Both the frozen-section autoradiography and organ distribution results indicated that analogue 2 has a potential as an adrenocortical imaging agent, having the highest degree of specific adrenal binding and best ratio of adrenal to organ uptake among the compounds studied.

    Emneord
    n. c. a. nucleophilic 18F-fluorination, [18F]alkyl MTO analogues, adrenocortical tumours
    HSV kategori
    Forskningsprogram
    Organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-89065 (URN)10.1016/j.nucmedbio.2009.01.014 (DOI)000266146700013 ()19423012 (PubMedID)
    Tilgjengelig fra: 2009-02-06 Laget: 2009-02-06 Sist oppdatert: 2017-12-14bibliografisk kontrollert
    3. Synthesis and in vitro evaluation of 18F-labelled di- and tri(ethylene glycol) metomidate esters
    Åpne denne publikasjonen i ny fane eller vindu >>Synthesis and in vitro evaluation of 18F-labelled di- and tri(ethylene glycol) metomidate esters
    2009 (engelsk)Inngår i: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 52, nr 7-8, s. 278-285Artikkel i tidsskrift (Fagfellevurdert) Published
    Abstract [en]

    By replacing the alkyl chain in a metomidate ester with F-18-labelled   di- or tri(ethylene glycol) chains, two F-18-labelled PET tracers, i.e.  2-(2-[F-18]fluoroethoxy)ethyl 1-[(1R)-1-phenylethyll-1   H-imidazole-5-carboxylate (1) and   2-[2-(2-[F-18]fluoroethoxy)-ethoxylethyl   1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate (2), were   synthesized. Two precursors, 2-(2-bromoethoxy)ethyl  1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate and   2-[2-(2-chloroethoxy)ethoxylethyl  1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate, were prepared and   used in one-step nucleophilic [F-18]fluorination reactions using   conventional and microwave heating. Organ distribution, frozen section   autoradiography and metabolite analysis were performed. The   decay-corrected radiochemical yields of 1 and 2 were 26 +/- 8 and 23   +/- 8%, respectively, when they were prepared using conventional   heating. By performing microwave heating, the reaction time could be   decreased and the yields of analogues 1 and 2 could be increased to 57   +/- 12 and 51 +/- 18%, respectively. Organ distribution studies in the   rat showed considerable uptake in the lungs, adrenals and liver. Both   compounds bound with low nonspecific binding (1: approx. 20-30%; 2:   2.9% or lower) to tissue from pig and human normal and pathologic   adrenals. Metabolite analyses were performed in rats after 5 and 30 min   for tracer 1 (20 +/- 6 and 2 +/- 1 %) and tracer 2 (27 +/- 5 and 6 +/-   4%). Both compounds are interesting candidates for the detection of   different types of adrenal disorders.

     

    Emneord
    n.c.a. nucleophilic 18F-fluorination, di- and tri(ethylene glycol), metomidate, analogues
    HSV kategori
    Identifikatorer
    urn:nbn:se:uu:diva-88794 (URN)10.1002/jlcr.1597 (DOI)000268690300029 ()
    Tilgjengelig fra: 2009-02-06 Laget: 2009-02-06 Sist oppdatert: 2017-12-14bibliografisk kontrollert
    4. 18F-Labelled vorozole analogues as PET tracer for aromatase
    Åpne denne publikasjonen i ny fane eller vindu >>18F-Labelled vorozole analogues as PET tracer for aromatase
    2008 (engelsk)Inngår i: J. Label Compd Radiopharm, nr 51, s. 207-212Artikkel i tidsskrift (Fagfellevurdert) Published
    Emneord
    n. c. a. nucleophilic 18f-fluorination, 18F-labelled VOZ nalaogues, aromatase
    HSV kategori
    Identifikatorer
    urn:nbn:se:uu:diva-16607 (URN)doi:10.1002/jlcr.1502 (DOI)
    Tilgjengelig fra: 2008-05-29 Laget: 2008-05-29 Sist oppdatert: 2011-01-11
    5. Pharmacological characterization of 18F-labeled vorozole analogues.
    Åpne denne publikasjonen i ny fane eller vindu >>Pharmacological characterization of 18F-labeled vorozole analogues.
    Vise andre…
    (engelsk)Manuskript (Annet vitenskapelig)
    Abstract [en]

    Two 18F-labeled analogues of vorozole ([18F]FVOZ and [18F]FVOO) have been developed as potential tools for the in vivo characterization of aromatase. The purpose of the project was to evaluate the pharmacological properties of these radioligands using a combination of in vitro binding and in vivo distribution studies in the rat and primate. Saturation binding studies with the radioligands in homogenates of rat ovary gave KD and Bmax values of 0.21 ± 0.1 nM and 210 ± 20 fmol/mg, respectively, for [18F]FVOZ, and 7.6 ± 1 nM and 293 ± 12 fmol/mg, respectively, for [18F]FVOO. Organ distribution studies in rats showed the highest accumulation in the adrenal glands, with standardized uptake values (SUVs) of 15 to 20, followed by ovaries and liver with SUVs of approximately 5. The SUVs in the remaining organs were between 0.5 and 1.5. There was probably some defluorination of both radioligands, as the accumulation of radioactivity in bone increased with time. The regional distribution in the brain was studied using ex vivo and in vitro autoradiography. In the brain, specific binding of both [18F]FVOZ and [18F]FVOO were found mainly in the amygdala. PET studies were performed in the Rhesus monkey, and these showed displaceable binding in the amygdala and the preoptic area of the hypothalamus. These studies suggest that [18F]FVOZ might be to be a suitable tracer for the study of aromatase in vitro and in vivo, and could be an alternative to [11C]vorozole in human PET-studies.

    Emneord
    aromatase, autoradiography, biodistribution, PET, rat brain, vorozole
    HSV kategori
    Forskningsprogram
    organisk kemi; medicin
    Identifikatorer
    urn:nbn:se:uu:diva-88793 (URN)
    Tilgjengelig fra: 2009-02-06 Laget: 2009-02-06 Sist oppdatert: 2018-01-13
    6. Automated synthesis of 18F-labelled analogues of etomidate, vorozole and harmine using commercial synthesizer TRACERLab FXFN
    Åpne denne publikasjonen i ny fane eller vindu >>Automated synthesis of 18F-labelled analogues of etomidate, vorozole and harmine using commercial synthesizer TRACERLab FXFN
    (engelsk)Manuskript (Annet vitenskapelig)
    Abstract [en]

    18F-Labelled analogues of three biologically interesting compounds, ethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate (ETO), 6-[(S)-(4-chlorophenyl)-(1H)-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole (VOZ) and 7-methoxy-1-methyl-9H-β-carboline (HAR) were synthesized by one-step nucleophilic fluorination. The 18F-labelled products were obtained with 20–30% isolated decay-corrected radiochemical yields and the radiochemical purities were over 99% in all cases. The labelling syntheses were performed using fully automated commercial synthesizer TRACERLab FXFN. The automation of the syntheses of these three promising PET tracers using a commercial synthesizer will make them accessible for clinical applications.       

    Emneord
    PET, TRACERLab FXFN, ETO, VOZ, HAR, automation
    HSV kategori
    Forskningsprogram
    organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-88789 (URN)
    Tilgjengelig fra: 2009-02-06 Laget: 2009-02-06 Sist oppdatert: 2018-01-13
  • 15.
    Garg, Neeraj
    et al.
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Westerlund, C
    Sundell, S
    Karlen, Anders
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Hallberg, Anders
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Preparation of cis-5-methoxy-and-7-methoxy-1-acetoxy-1,2,3,4,4a,10a-hexahydro-9(10H)-phenanthrenone. An epoxide-arene reaction involving a selective 1,2-alkyl shift rearrangement1996Inngår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 52, nr 48, s. 15209-15224Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The preparation of cis-1α-acetoxy-7-methoxy-1,2,3,4,4a,10a-hexahydro-9(10H)- phenanthrenone 5 was accomplished starting from 6-methoxy-1-tetralone. Reduction of 7-methoxy-1,2,3, 4,9,10-hexahydro-1-oxo-phenanthrene 8, acetylation and subsequent oxidation delivered 5. Application of an analogus procedure to the preparation of cis-1β-acetoxy-5-methoxy-1,2,3,4,,4a,10a-hexahydro-9(10H)- phenanthrenone 6 was not feasible. A more elaborate route was developed for the synthesis of compound 6, where an epoxide-arene reaction involving a 1,2-alkyl shift rearrangement, constituted a highly selective key transformation.

    The compounds 5 and 6 were prepared. A route was developed for the synthesis of compound 6, where an epoxide-arene reaction involving a 1,2-alkyl shift rearrangement, constituted a highly selective key transformation.

  • 16.
    Georgsson, Jennie
    et al.
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Sköld, Christian
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Plouffe, Bianca
    Lindeberg, Gunnar
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Botros, Milad
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för farmaceutisk biovetenskap, Avdelningen för biologisk beroendeforskning.
    Larhed, Mats
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Nyberg, Fred
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för farmaceutisk biovetenskap, Avdelningen för biologisk beroendeforskning.
    Gallo-Payet, Nicole
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Karlén, Anders
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Hallberg, Anders
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Angiotensin II Pseudopeptides Containing 1,3,5-Trisubstituted Benzene Scaffolds with High AT2 Receptor Affinity2005Inngår i: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 48, nr 21, s. 6620-6631Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Two 1,3,5-trisubstituted aromatic scaffolds intended to serve as γ-turn mimetics have been synthesized and incorporated in five pseudopeptide analogues of angiotensin II (Asp-Arg-Val-Tyr-Ile-His-Pro-Phe), replacing Val-Tyr-Ile, Val-Tyr, or Tyr-Ile. All the tested compounds exhibited nanomolar affinity for the AT2 receptor with the best compound (3) having a Ki of 1.85 nM. Four pseudopeptides were AT2 selective, while one (5) also exhibited good affinity for the AT1 receptor (Ki = 30.3 nM). This pseudopeptide exerted full agonistic activity in an AT2 receptor induced neurite outgrowth assay but displayed no agonistic effect in an AT1 receptor functional assay. Molecular modeling, using the program DISCOtech, showed that the high-affinity ligands could interact similarly with the AT2 receptor as other ligands with high affinity for this receptor. A tentative agonist model is proposed for AT2 receptor activation by angiotensin II analogues. We conclude that the 1,3,5-trisubstituted benzene rings can be conveniently prepared and are suitable as γ-turn mimics.

  • 17.
    Gogoll, Adolf
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Grennberg, Helena
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Structural Assignment of  σ-π-Palladium Complexes by 2D NMR1993Inngår i: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 31, nr 10, s. 954-959Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A series of (σ-π)palladium complexes derived from cyclooctadiene were investigated by 1H, 13C and 19F NMR. The stereochemical assignment was based on intramolecular NOEs in conjunction with molecular modelling and semi-empirical methods, and confirmed by interligand NOEs in nitrogen chelate complexes derived from the title compounds. The nitrogen chelating ligands are involved in a rotation with respect to the ligand-palladium axis.

  • 18.
    Gogoll, Adolf
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen.
    Grennberg, Helena
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Axen, Andreas
    Uppsala universitet.
    (π-Allyl)palladium complexes with N,N'-diphenylbispidinone derivatives as a new type of chelating nitrogen ligand: Complexation studies, spectroscopic properties, and an x-ray structure of (3,7-diphenyl-1,5-dimethylbispidinone)[(1,3-η(3)-propenyl)-pal1997Inngår i: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 16, nr 6, s. 1167-1178s. 1167-1178Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A series of 3,7-diazabicyclo[3.3.1]nonane (bispidine) derivatives have been synthesized, and their properties as bidentate nitrogen ligands for (pi-allyl)palladium complexes have been investigated. Complexes of these ligands and of N,N'-diphenylpiperazin

  • 19.
    Gogoll, Adolf
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gundersen, Lise-Lotte
    Department of Chemistry, University of Oslo.
    Rise, Frode
    Department of Chemistry, University of Oslo.
    Valli, Mats
    Alkylation and Convalent Adduct Formation of 2-Oxopurine1993Inngår i: Heterocycles, ISSN 0385-5414, E-ISSN 1881-0942, Vol. 36, nr 2, s. 231-235Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    2-Oxopurine reacted with benzyl bromide and ethanol to give the covalent adduct 1,3,7-tribenzyl-6-ethoxy-2-oxopurine, as well as dibenzylated products. Carbon-carbon bond formation was observed in the reaction between 2-oxopurine, dry silica gel, and benzyl bromide, giving rise to 6-hydroxy-1,3,8-tribenzyl-2-oxopurine.

  • 20.
    Gogoll, Adolf
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Plobeck, Niklas A.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Comparison of one- and two-dimensional techniques in the unambiguous 13C NMR spectral assignment of ellipticine and related indole derivatives1990Inngår i: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 28, s. 635-641Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The 13C NMR spectra of several indole derivatives have been completely assigned by reverse detected one-bond and long-range CH correlation spectra (HMQC) and by selective INEPT experiments. The resolution and sensitivity of the two techniques are discussed. As a result, the literature assignments for the previously known compounds have been revised.

  • 21.
    Gogoll, Adolf
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Tanner, David
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Complete 1H and 13C NMR spectral assignment of venturicidin A by 2D NMR spectroscopy1989Inngår i: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 27, nr 9, s. 863-871Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    After correlation of the majority of signals by COSY and one-bond heteronuclear correlation, the complete assignment of the 1H and 13C NMR spectra of the macrolide antibiotic venturicidin A required the application of long-range CH coupling information. This was accessible by the COLOC-S and selective INEPT experiments, and the sensitivity of these experiments is discussed. Steric information was obtained from a NOESY spectrum, and the solution structure compared with that in the crystal.

  • 22.
    Gogoll, Adolf
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Örnebro, Jörgen
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen.
    Grennberg, Helena
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Bäckvall, Jan-Erling
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Mechanism of Apparent π-Allyl Rotation in (π-Allyl)Palladium Complexes with Bidentate Nitrogen Ligands1994Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 116, nr 8, s. 3631-3632Artikkel i tidsskrift (Fagfellevurdert)
  • 23.
    Grennberg, Helena
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Bäckvall, Jan-Erling
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Acid‑Induced Transformation of Palladium(0)­‑Benzoquinone Complexes to Palladium(II) and Hydroquinone1993Inngår i: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 12, nr 5, s. 1790-1793Artikkel i tidsskrift (Fagfellevurdert)
  • 24.
    Grennberg, Helena
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Bäckvall, Jan-Erling
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Use of Sulfoxides as Co‑catalysts in the Palladium‑Quinone‑Catalyzed 1,4‑Diacetoxylation of 1,3‑Dienes: An Example of Ligand‑Accelerated Catalysis1991Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 56, nr 20, s. 5811-5811Artikkel i tidsskrift (Fagfellevurdert)
  • 25.
    Gundersen, Lise-Lotte
    et al.
    UNIV OSLO, DEPT CHEM, POB 1033, N-0315 OSLO, NORWAY.
    Benneche, Tore
    UNIV OSLO, DEPT CHEM, POB 1033, N-0315 OSLO, NORWAY.
    Rise, Frode
    UNIV OSLO, DEPT CHEM, POB 1033, N-0315 OSLO, NORWAY.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Undheim, Kjell
    UNIV OSLO, DEPT CHEM, POB 1033, N-0315 OSLO, NORWAY.
    Regiochemistry and Stereochemistry in Pd(0)‑Catalyzed Allylic Alkylation of Nucleoside Bases1992Inngår i: Acta Chemica Scandinavica, ISSN 0904-213X, E-ISSN 1902-3103, Vol. 46, s. 761-771Artikkel i tidsskrift (Fagfellevurdert)
  • 26.
    Helander, Anders
    et al.
    Uppsala University, Department of Zoophysiology.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Mechanisms for Plasma‑Mediated Activation of Human Blood Cell Aldehyde Dehydrogenase1992Inngår i: Biochimica et Biophysica Acta. Molecular Cell Research, ISSN 0167-4889, E-ISSN 1879-2596, Vol. 1136, nr 3, s. 259-264Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Aldehyde dehydrogenase (ALDH; EC 1.2.1.3) activity assays were carried out on isolated human blood cells in phosphate-buffered saline (PBS) and in PBS mixed with human plasma. In assays with intact erythrocytes or sonicated leukocytes, the presence of 50% (v/v) or greater of plasma in the reaction mixtures produced a 2-fold increase in the rate of aldehyde oxidation. In corresponding assays with sonicated erythrocyte samples, the ALDH activity was enhanced on an average 1.5-fold, whereas a slight decrease was observed in assays with intact leukocytes. The ALDH inhibitor disulfiram almost completely abolished the enzyme activity both in the absence and presence of plasma. In assays with sonicated leukocytes, the activation effect could be antagonized by EDTA, indicating that it was caused largely by divalent cations. With sonicated erythrocytes, a significantly reduced ALDH activity was found only with the highest concentration of EDTA tested, and since a similar reduction was obtained also when plasma was omitted, the plasma-mediated activation of erythrocyte ALDH was suggested to be due to a different mechanism. After separation of plasma by gel filtration, an active fraction was identified by GC-MS and 1H-NMR to contain pyruvic acid, lactic acid and glucose. When tested at physiological plasma concentrations, pyruvic acid caused an increase in erythrocyte ALDH activity similar to that obtained with plasma, while lactic acid and glucose did not. Pyruvic acid did not activate the leukocyte ALDH. Based on these results, it is indicated that the plasma-mediated activation of erythrocyte ALDH is due to pyruvic acid, which reoxidizes NADH via lactate dehydrogenase (EC 1.1.1.27) and, thereby, increases the rate of dissociation of NADH from the terminal enzyme-NADH complex, the rate-limiting step in the ALDH pathway.

  • 27.
    Holmberg, Pär
    et al.
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi.
    Karlsson, John
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi. Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen, Avdelningen för organisk kemi.
    Enzymatic Kinetic Resolution of 1-(3-furyl)-3-buten-1ol2005Inngår i: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 16, s. 2397-2399Artikkel i tidsskrift (Annet vitenskapelig)
    Abstract [en]

    The enzymatic kinetic resolution of 1-(3-furyl)-3-buten-1-ol was investigated via the enantioselective hydrolysis of the corresponding acetate. Pseudomonas fluorescens (Fluka) was found to give the highest enantiomeric ratios of the 11 lipases screened. At 51% conversion, the ee value (eep) for the product was found to be 89%, giving an enantiomeric ratio (Ep) of 58, while the ee value (ees) for the substrate was 89%, giving an enantiomeric ratio (Ep) of 38.

  • 28.
    Jafri, Hassan
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Experimentell fysik.
    Blom, Tobias
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Experimentell fysik.
    Widenqvist, Erika
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för materialkemi, Oorganisk kemi.
    Carva, Karel
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Fysiska sektionen, Institutionen för fysik och astronomi, Materialteori.
    Sanyal, Biplab
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Fysiska sektionen, Institutionen för fysik och astronomi, Materialteori.
    Eriksson, Olle
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Fysiska sektionen, Institutionen för fysik och astronomi, Materialteori.
    Grennberg, Helena
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Jansson, Ulf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för materialkemi, Oorganisk kemi.
    Quinlan, R.A.
    College of William and Mary, US.
    Holloway, B.
    Luna Innovations Incorporated.
    Surpi, Alessandro
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Experimentell fysik.
    Leifer, Klaus
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Experimentell fysik.
    Control of Conductivity in Graphene by Formation of Defects2008Inngår i: AVS 55th International Symposium & Exhibition 2008, October 19-24, Boston, USA, 2008Konferansepaper (Fagfellevurdert)
    Abstract [en]

    Due to their large surface areas, the conductivity of graphene and carbonnano-sheets depends strongly on their chemical environment. This is thebase for future environmental sensors containing graphene sheets. Here, abinitiocalculations propose a possibility of conductivity increase. In theexperiment, a 1-2 orders of magnitude increase of the conductivity isobserved experimentally on sub-nanometTe carbon nano-sheets by using anin-situ nano-manipulation set-up. The conductivity of the graphene sheetswas assessed from first-principle simulations. Insertion of defects in thegraphene sheets can lead to a strong increase of the conductivity of singlegraphene sheets. To study this result experimentally, we carried outconductivity measurements on sub-nanometre graphene nano-sheets that aredeposited on W -substrates by radio-frequency plasma-enhanced chemicalvapour deposition. This deposition process creates free-standingmicrometer-sized carbon nano-sheets with sub-nanometre thickness. Thesenano-sheets were exposed to an acid treatment. It has been shown recentlythat such acid treatment creates defects in these sheets. Using a nanomanipulatorinside a scanning electron microscope, we individuallycontacted the nano-sheets and measured their resistance as a function oftheir functionalization. From more than 1000 measurements we obtain a 1-2order of magnitude increase of conductivity in the functionalised carbonnano-sheets as compared to just water treated or untreated carbon nanosheets.This result corresponds well to the conductivity change obtainedfrom theory. This study makes it possible to create environmental sensorsbased on graphene like carbon nano-sheets.

  • 29.
    Johannesson, P
    et al.
    Uppsala universitet.
    Lindeberg, G
    Uppsala universitet.
    Tong, WM
    Uppsala universitet.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Synnergren, B
    Uppsala universitet.
    Nyberg, F
    Uppsala universitet.
    Karlen, A
    Uppsala universitet.
    Hallberg, A
    Uppsala universitet.
    Angiotensin II analogues encompassing 5,9-and 5,10-fused thiabicycloalkane tripeptide mimetics1999Inngår i: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 42, nr 22, s. 4524-4537s. 4524-4537Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A simple experimental procedure on solid phase for the construction of new tripeptidic 5,9- and 5,10-fused thiazabicycloalkane scaffolds that adopt beta-turns has been developed. This N-terminal-directed bicyclization, relying on masked aldehyde precurso

  • 30.
    Johannesson, Petra
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen.
    Lindeberg, Gunnar
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Johansson, Anja
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Nikiforovich, Gregory V
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Synnergren, Barbro
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för farmaceutisk biovetenskap.
    Le Greves, Madeleine
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för farmaceutisk biovetenskap.
    Nyberg, Fred
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för farmaceutisk biovetenskap, Avdelningen för biologisk beroendeforskning.
    Karlen, Anders
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Hallberg, Anders
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Vinyl sulfide cyclized analogues of angiotensin II with high affinity and full agonist activity at the AT(1) receptor2002Inngår i: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 45, nr 9, s. 1767-1777Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Vinyl sulfide cyclized analogues of the octapeptide angiotensin II that are structurally related to the cyclic disulfide agonist c[Hcy(3,5)]Ang II have been prepared. The synthesis relies on the reaction of the mercapto group of a cysteine residue in position 3 with the formyl group of allysine incorporated in position 5 of angiotensin II. A mixture of the cis and the trans isomers was formed, and these were separated and isolated by RP-HPLC. Thus, the three-atom CH(2)[bond]S[bond]S element of the AT(1) receptor agonist c[Hcy(3,5)]Ang II has been displaced by a bioisosteric three-atom S[bond]CH[double bond]CH element. A comparative conformational analysis of the 13-membered ring systems of c[Hcy(3,5)]Ang II and the 13-membered cyclic vinyl sulfides with cis and trans configuration, respectively, suggested that all three systems adopted very similar low-energy conformations. This similarity was also reflected in the bioactivity. Both of the compounds that contained the ring systems encompassing the cis or trans vinyl sulfide elements between positions 3 and 5 exhibited K(i) values less than 2 nM and exerted full agonism at the AT(1) receptor. In contrast, vinyl sulfide cyclization involving the amino acid residues 5 and 7 rendered inactive compounds. The cyclic vinyl sulfides that have agonist activity were both shown to possess low-energy conformers compatible with the previously proposed 3D model for the bioactive conformation of Ang II.

  • 31.
    Kocovsky, Pavel
    et al.
    Uppsala universitet.
    Dunn, Victoria
    Uppsala universitet.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Langer, Vratislav
    Uppsala universitet.
    An approach toward the triquinane-type skeleton via reagent-controlled skeletal rearrangements. A facile method for protection-deprotection of organomercurials, tuning the selectivity of Wagner-Meerwein migrations, and a new route to annulated lactones1999Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 64, nr 1, s. 101-119s. 101-119Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Nonlinear triquinane-type building blocks have been synthesized using three strategic steps, namely, (1) Hg2+-mediated opening of a cyclopropane ring involving a skeletal rearrangement (3 --> 8), (2) an intramolecular organometallic addition across a C=O

  • 32.
    Kočovský, Pavel
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Pour, Milan
    CZECHOSLOVAK ACAD SCI, INST ORGAN CHEM & BIOCHEM, CS-16610 PRAGUE 6, CZECH REPUBLIC.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Hanuš, Vladimir
    CZECHOSLOVAK ACAD SCI, J HEYROVSKY INST PHYS CHEM & ELECTROCHEM, CS-18223 PRAGUE 8, CZECH REPUBLIC .
    Smrcina, M.
    CZECHOSLOVAK ACAD SCI, J HEYROVSKY INST PHYS CHEM & ELECTROCHEM, CS-18223 PRAGUE 8, CZECH REPUBLIC .
    Corner Attack on Cyclopropane by Thallium(III) Ions: A Highly Stereospecific Cleavage and Skeletal Rearrangement of 3a,5‑Cyclo‑5a‑cholestan‑6a‑ol1990Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 112, nr 18, s. 6735-6737Artikkel i tidsskrift (Fagfellevurdert)
  • 33.
    Kočovský, Pavel
    et al.
    UNIV LEICESTER, DEPT CHEM, LEICESTER LE1 7RH, ENGLAND .
    Šrogl, Jiri
    Pour, Milan
    AUSTRALIAN NATL UNIV, RES SCH CHEM, CANBERRA.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Corner Opening of Cyclopropane by Mercury(II) and Thallium(III) and Transmetallation of the Intermediate Organomercurials: A  Novel, Stereoselective Approach to Cyclobutanes and Cyclopropanes1994Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 116, nr 1, s. 186-197Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The reactivity of the two isoelectronic cations (Hg2+ and T P ) toward the cyclopropane ring is compared, and further evidence for the exclusive corner selectivity for Hg2+ is provided by isotope labeling. Cleavage of cyclopropyl derivative 1 with Hg(NO3)2, followed by KBr quenching, afforded the stable, rearranged organomercurial 3,  whose transmetalation has been studied. Whereas reaction of 3 with Pd(I1) afforded lactol 4,  treatment with MezCuLi resulted in the formation of cyclobutanol derivative (3 - 29);  analogous conjugate addition has also been accomplished (32 - 35). Similarly, the organomercurial 22, obtained from 21  as the major product on the Hg(I1)-mediated ringopening, reacted with MezCuLi or AlC13 to give the ring-closure product 21. These reactions representa novel method for the stereoselective construction of four- and three-membered rings. The stereochemistry of the key steps of these transformations has been established by using stereospecifically deuterated substrates lb, 3b, 21b, and 22b.

  • 34.
    Kočovský, Pavel
    et al.
    UNIV LEICESTER, DEPT CHEM, LEICESTER LE1 7RH, ENGLAND .
    Šrogl, Jiří
    UNIV LEICESTER, DEPT CHEM, LEICESTER LE1 7RH, ENGLAND .
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Hanuš, Vladimír
    CZECHOSLOVAK ACAD SCI, J HEYROVSKY INST PHYS CHEM & ELECTROCHEM, CS-18223 PRAGUE 8.
    Polášek, Miroslav
    CZECHOSLOVAK ACAD SCI, J HEYROVSKY INST PHYS CHEM & ELECTROCHEM, CS-18223 PRAGUE 8.
    Transmetalation with Pd(II) of an Organomercurial Arising from the Hg(II)‑Mediated Cyclopropane Cleavage: Tuning of the Reactivity by Ligands and a Novel, Intramolecular Redox Reaction1992Inngår i: Journal of the Chemical Society, Chemical Communications, ISSN 0022-4936, Vol. 15, s. 1086-1087Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The cleavage of the fused-ring cyclopropane hydroxy derivative 1 by means of HgII is highly stereoselective and gives a rearranged organomercurial 3, transmetallation of which with PdII can be controlled by ligands to afford either lactol 4 or acid 8; the latter compound is formed via an intramolecular insertion of Pd into the C–H bond (67), as evidenced by isotopic labelling.

  • 35. Kuhn, Christian
    et al.
    Lindeberg, Gunnar
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Hallberg, Anders
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Schmidt, Boris
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Fmoc protected peptide mimetic based on a cyclohexane framework and incorporation into angiotensin II1997Inngår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 53, nr 37, s. 12497-12504Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    1,3,5-syn substituted cyclohexane based amino acids have been prepared and incorporated into synthetic peptides to serve as scaffold mimicking the Val-Tyr-Ile sequence of angiotensin II. The conformationally constrained tripeptide mimetic holds potential use as a γ-turn replacement.

  • 36.
    Kumlien, Eva
    et al.
    Uppsala universitet, Medicinska vetenskapsområdet, Medicinska fakulteten, Institutionen för neurovetenskap. Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Nilsson, A
    Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Hagberg, G
    Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Langstrom, B
    Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Bergstrom, M
    Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    PET with 11C-deuterium-deprenyl and 18F-FDG in focal epilepsy2001Inngår i: Acta Neurologica Scandinavica, Vol. 103, s. 360-Artikkel i tidsskrift (Fagfellevurdert)
  • 37.
    Lindman, Susanna
    et al.
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Lindeberg, Gunnar
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Nyberg, Fred
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för farmaceutisk biovetenskap, Avdelningen för biologisk beroendeforskning.
    Karlen, Anders
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Hallberg, Anders
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Synthesis, receptor binding affinities and conformational properties of cyclic methylenedithioether analogues of angiotensin II2001Inngår i: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 9, nr 3, s. 763-772Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Cyclic 12-, 13- and 14-membered ring angiotensin II analogues related to disulfides but encompassing methylenedithioether bridges have been prepared. The affinity data from these derivatives were compared to those from the disulfides. The methylenedithioether analogues displayed good binding affinities to rat liver AT1 receptors although in most cases somewhat lower than their disulfide counterparts. One of the methylenedithioethers with a 13-membered ring system demonstrated the highest binding affinity among the thioethers. Theoretical conformational analysis of model compounds of the two series were performed suggesting a similarity between the disulfide and the corresponding methylenedithioether analogues and also between the ring size homologues. This analysis also suggested that some of the model compounds were prone to adopt inverse γ-turn conformations, which was further supported by use of NMR spectroscopy of the 12-membered ring analogue in the series. The easily executed methylenedithioether cyclization should constitute a valuable complement to the common disulfide methodology for fine-tuning and for probing the bioactive conformation of peptides.

  • 38.
    Maslankiewicz, Andrzej
    et al.
    WROCLAW UNIV, INST CHEM, PL-50383 WROCLAW, POLAND .
    Wyszomirski, Miroslaw
    WROCLAW UNIV, INST CHEM, PL-50383 WROCLAW, POLAND .
    Boryczka, Stanislaw
    WROCLAW UNIV, INST CHEM, PL-50383 WROCLAW, POLAND .
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Glowiak, Tadeusz
    WROCLAW UNIV, INST CHEM, PL-50383 WROCLAW, POLAND .
    Structure of 4-Substituted 3,4'-Diquinolinyl Sulfides Studied by 1H and 13C NMR and X-Ray Analysis1993Inngår i: Phosphorus Sulfur and Silicon and the Related Elements, ISSN 1042-6507, E-ISSN 1563-5325, Vol. 74, s. 429-430Artikkel i tidsskrift (Fagfellevurdert)
  • 39.
    Maslankiewicz, Andrzej
    et al.
    SILESIAN MED ACAD, DEPT ORGAN CHEM, JAGIELLONSKA STR 4, PL-41200 SOSNOWIEC, POLAND .
    Wyszomirski, Miroslaw
    SILESIAN MED ACAD, DEPT ORGAN CHEM, JAGIELLONSKA STR 4, PL-41200 SOSNOWIEC, POLAND .
    Glowiak, Tadeusz
    Institute of Chemistry, University of Wroclaw, WROCLAW, POLAND.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Azinylsulfides. Part XV. X‑Ray Structure and NMR Assignment of 3,4‑Dimethylthioquinoline1991Inngår i: Journal of crystallographic and spectroscopic research, ISSN 0277-8068, Vol. 21, nr 5, s. 559-565Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The title compound (C11H11NS2) is monoclinic:P21/c,a=15.200(4),b=14.644(4),c=10.098(3),Z=8. The structure was solved by direct methods, and refined to anR value of 0.047 with 2886 independent reflections. There are two nonequivalent molecules in the unit cell. BothS-methyl groups have different spatial orientation: the B-methyl group side-chain is approximately coplanar with the pyridine ring and turned to the ortho-position, but r-methyl group side-chain is turned over this ring. Both1H and13C NMR spectra were assigned using 1D and 2D experiments. The NOE measurements are consistent with inter-proton distances from X-ray data.

  • 40.
    Matsson, Olle
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi. Institutionen för fysikalisk och analytisk kemi, Kvantkemi.
    Frändberg, Åke
    Hedlund, Monica
    Lunell, Sten
    Fysiska sektionen, Institutionen för kvantkemi. Institutionen för biokemi och organisk kemi, Organisk kemi. Institutionen för fysikalisk och analytisk kemi, Kvantkemi.
    Sedin, Gunnar
    LIBENS MERITO - Festskrift till Stig Strömholm på sjuttioårsdagen 16 september 20012001Bok (Annet vitenskapelig)
  • 41. Mazuela, Javier
    et al.
    Norrby, Per-Ola
    Andersson, Pher G.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Pamies, Oscar
    Dieguez, Montserrat
    Pyranoside Phosphite-Oxazoline Ligands for the Highly Versatile and Enantioselective Ir-Catalyzed Hydrogenation of Minimally Functionalized Olefins: A Combined Theoretical and Experimental Study2011Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 133, nr 34, s. 13634-13645Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A modular set of phosphite-oxazoline (P,N) ligands has been applied to the title reaction. Excellent ligands have been identified for a range of substrates, including previously challenging terminally disubstituted olefins, where we now have reached enantioselectivities of 99% for a range of substrates. The selectivity is best for minimally functionalized substrates with at least a moderate size difference between geminal groups. A DFT study has allowed identification of the preferred pathway. Computational prediction of enantioselectivities gave very good accuracy.

  • 42. Mazuela, Javier
    et al.
    Tolstoy, Päivi
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
    Pamies, Oscar
    Andersson, Pher G.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Dieguez, Montserrat
    Phosphite-oxazole/imidazole ligands in asymmetric intermolecular Heck reaction2011Inngår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 9, nr 3, s. 941-946Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    We describe the application of a new class of ligands -the phosphite-oxazole/imidazole (L1-L5a-g) in asymmetric intermolecular Pd-catalyzed Heck reactions under thermal and microwave conditions. These ligands combine the advantages of the oxazole/imidazole moiety with those of the phosphite moiety: they are more stable than their oxazoline counterparts, less sensitive to air and other oxidizing agents than phosphines and phosphinites, and easy to synthesize from readily available alcohols. The results indicate that activities, regio- and enantioselectivities, are highly influenced by the type of nitrogen donor group (oxazole or imidazole), the oxazole and biaryl-phosphite substituents and the axial chirality of the biaryl moiety of the ligand. By carefully selecting the ligand components, we achieved high activities, regio- (up to 99%) and enantioselectivities (up to 99%) using several triflate sources. Under microwave-irradiation conditions, reaction times were considerably shorter (from 24 h to 30 min) and regio- and enantioselectivities were still excellent.

  • 43.
    Maślankiewicz, Andrzej
    et al.
    Silesian School of Medicine, Sosnowiec, Poland.
    Pluta, Krystian
    Silesian School of Medicine, Sosnowiec, Poland.
    Wyszomirski, Mirosław
    Silesian School of Medicine, Sosnowiec, Poland.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Maślankiewicz, Maria J.
    Silesian Univ, Inst Chem, Katowice, Poland .
    Complete assignment of the 1H and 13C NMR spectra of thioquinanthrene and isothioquinanthrene1998Inngår i: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 36, nr 1, s. 73-75Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The proton and carbon chemical shifts and the coupling constants (n)J(H,H) and (n)J(C,H) of thioquinanthrene and isothioquinanthrene were completely assigned from COSY, HETCOR and INEPT studies.

  • 44.
    Nordvall, Gunnar
    et al.
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Sundquist, Staffan
    KABI PHARM AB, DEPT RECEPTOR PHARMACOL UROL GYNAECOL, S-11287 STOCKHOLM, SWEDEN.
    Glas, Gunilla
    KABI PHARM AB, DEPT RECEPTOR PHARMACOL UROL GYNAECOL, S-11287 STOCKHOLM, SWEDEN.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Nilvebrant, Lisbeth
    KABI PHARM AB, DEPT RECEPTOR PHARMACOL UROL GYNAECOL, S-11287 STOCKHOLM, SWEDEN.
    Hacksell, Uli
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
    Analogs of the Muscarinic Agent 2'‑Methylspiro(1‑azabicyclo[2.2.2]octane)­‑3,4'‑[1,3]dioxolane (AF30): Synthesis and Pharmacology1992Inngår i: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 35, nr 9, s. 1541-1550Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A number of tetrahydrofuran analogues of 2'-methylspiro[1-azabicyclo[2.2.2]octane-3,4'-[1,3]dioxolane] ( 1) have been prepared with the aim to obtain information about the relative importance of each of the oxygens in 1 for efficacy and for selectivity. In addition, the dimethyl and deamethyl doguea of 1 &re prepared. The new compounds were compared to cis- and trans-1 with regard to their ability to displace (-)-[3H]-3-quinuclidinyl benzilate ((-)-[3H]QNB) from muscarinic receptors in cerebral cortex, heart, parotid gland, and urinary bladder from  guinea pigs. Functioinal studies were made on isolated guinea pig bladder and ileum. The new compounds exhibited both lower affmity and efficacy thancis-1.Aconformational studywasperformed,and the effects of steric and electronic factors on the biological activity of the compounds are discussed.

  • 45.
    Nájera, Carmen
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Yus, Miguel
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Karlsson, Ulrika
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Bäckvall, Jan-Erling
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Nitroselenation of conjugated dienes: Preparation of 3,4-epoxy-3-nitro-1-alkenes1990Inngår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 31, nr 29, s. 4199-4202Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Conjugated dienes were transformed to synthetically useful 3,4-epoxy-3-nitro-1-alkenes via a nitroselenation-oxidation sequence.

    Conjugated dienes were transformed to synthetically useful 3,4-epoxy-3-nitroalkenes via a nitroselenation-oxidation sequence.

  • 46.
    Orlova, Anna
    et al.
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Medicinska fakulteten, Institutionen för onkologi, radiologi och klinisk immunologi, Enheten för biomedicinsk strålningsvetenskap.
    Bruskin, Alexander
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Medicinska fakulteten, Institutionen för onkologi, radiologi och klinisk immunologi, Enheten för biomedicinsk strålningsvetenskap.
    Sivaev, Igor
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Sjöberg, Stefan
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Lundqvist, Hans
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Medicinska fakulteten, Institutionen för onkologi, radiologi och klinisk immunologi, Enheten för biomedicinsk strålningsvetenskap.
    Tolmachev, Vladimir
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Medicinska fakulteten, Institutionen för onkologi, radiologi och klinisk immunologi, Enheten för biomedicinsk strålningsvetenskap.
    Radio-iodination of monoclonal antibody using potassium [125I]-(4-isothiocyanatobenzylammonio)-iodo-decahydro-closo-dodecaborate (iodo-DABI)2006Inngår i: Anticancer Research, ISSN 0250-7005, E-ISSN 1791-7530, Vol. 26, nr 2A, s. 1217-1223Artikkel, omtale (Annet vitenskapelig)
    Abstract [en]

    BACKGROUND:

    Negatively-charged polyhedral boron clusters can be easily halogenated with highly stable boron-halogen bonds and are promising in radionuclide diagnostics and cancer therapy.

    MATERIALS AND METHODS:

    The radio-iodination conditions for the closo-dodecaborate anion and for the conjugation of its labeled isothiocyanatobenzylammonio derivative to the monoclonal antibody (mAb) were optimized.

    RESULTS:

    The labeling yield was about 90% and the overall conjugation yield was 55-60%. The in vitro stability of the radio-iodinated mAb was good under physiological and non-physiological conditions. The immunoreactivity of the labeled mAb (SK-BR-3 cells) was retained in the one-pot two-step labeling.

    CONCLUSION:

    Negatively-charged polyhedral boron clusters can be used for indirect radio-iodination of mAbs.

  • 47. Pamies, Oscar
    et al.
    Andersson, Pher G.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Dieguez, Montserrat
    Asymmetric Hydrogenation of Minimally Functionalised Terminal Olefins: An Alternative Sustainable and Direct Strategy for Preparing Enantioenriched Hydrocarbons2010Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, nr 48, s. 14232-14240Artikkel, forskningsoversikt (Fagfellevurdert)
    Abstract [en]

    This account discusses the progress made in the asymmetric hydrogenation of minimally functionalised terminal olefins as a new, alternative, sustainable and direct strategy for preparing enantioenriched hydrocarbons. It discusses the latest development in catalyst design, from the initial discovery of lanthanide catalytic precursors, through the use of transition-metal/diphosphine iminophosphorane precursors, to the successful iridium/P,N catalytic systems.

  • 48.
    Paptchikhine, Alexander
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Itto, Kaori
    Andersson, Pher G.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Sequential Birch reaction and asymmetric Ir-catalyzed hydrogenation as a route to chiral building blocks2011Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 47, nr 13, s. 3989-3991Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A range of 1,2,4-trisubstituted cyclohexadienes obtained from the Birch reaction were hydrogenated asymmetrically to produce synthetically valuable chiral compounds in high enantio- and diastereoselectivity.

  • 49.
    Pettersson, Helena
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Bäckvall, Jan-Erling
    Epoxidation of 5-(tosylamido)-3-hexen-2-ol derivatives. Stereochemical assignment of product configuration by NMR and molecular mechanics studies1992Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 57, nr 22, s. 6025-6031Artikkel i tidsskrift (Fagfellevurdert)
  • 50.
    Sawadjoon, Supaporn
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Samec, Joseph S. M.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis2011Inngår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 9, nr 7, s. 2548-2554Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The synthesis of N-aryl, N-tosyl, and N-alkyl pyrrolines from allyl alcohols and amines has been developed. The reaction sequence includes a palladium-catalyzed allylation step in which non-manipulated allyl alcohol is used to generate the diallylated amine in good to excellent yield. An excess of allyl alcohol was necessary for efficient diallylation of the amine, where the excess alcohol could be recycled three times. For aryl and tosyl amines, Pd[P(OPh)(3)](4) was used and for benzyl and alkyl amines a catalytic system comprising Pd(OAc)(2), (PBu3)-Bu-n, and BEt3 was used. Both the electronic properties and the steric influence of the amine affected the efficiency of the allylation. The isolated diallylated amines were transformed into their corresponding pyrrolines by ring-closing metathesis catalyzed by (H(2)IMes)(PCy3)Cl2RuCHPh in good to excellent yield. A one-pot reaction was developed in which aniline was transformed into the corresponding pyrroline without isolating the diallylated intermediate. This one-pot reaction was successfully scaled-up to 1 mL of aniline in which the N-phenyl pyrroline was isolated in 95% yield. The versatility of the reaction in which 3-methyl-1-phenyl pyrroline was prepared in two-steps was demonstrated.

12 1 - 50 of 65
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