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  • 1.
    Ahlgren, Joakim
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry.
    Reitzel, Kasper
    Tranvik, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Evolution, Limnology.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Rydin, Emil
    Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Evolution, Limnology.
    Degradation of organic phosphorus compounds in anoxic Baltic Sea sediments: A P-31 nuclear magnetic resonance study2006In: Limnology and Oceanography, ISSN 0024-3590, E-ISSN 1939-5590, Vol. 51, no 5, p. 2341-2348Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Liedberg, Bo
    Assembly of polypeptide-functionalized gold nanoparticles through a heteroassociation- and folding-dependent bridging2008In: Nano letters (Print), ISSN 1530-6984, E-ISSN 1530-6992, Vol. 8, no 8, p. 2473-2478Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Berggren, Gustav
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Photochemistry and Molecular Science.
    Ott, Sascha
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Photochemistry and Molecular Science, Molecular Biomimetics.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Synthesis and IR Spectroelectrochemical Studies of a [60]Fulleropyrrolidine-(tricarbonyl)chromium Complex: Probing C-60 Redox States by IR Spectroscopy2011In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 11, p. 1744-1749Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    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 set2011In: Analytical and Bioanalytical Chemistry, ISSN 1618-2642, E-ISSN 1618-2650, Vol. 400, no 6, p. 1653-1664Article, review/survey (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Applied Materials Sciences.
    Jafri, Hassan
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Applied Materials Sciences.
    Di Cristo, Valentina
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Applied Materials Sciences.
    Carva, Karel
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Materials Theory.
    Possnert, Göran
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, High Energy Physics.
    Sanyal, Biplab
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Materials Theory.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Jansson, Ulf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Materials Chemistry, Inorganic Chemistry.
    Eriksson, Olle
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Materials Theory.
    Leifer, Klaus
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Applied Materials Sciences.
    Conduction properties of graphene as a function of ion irradiation and acid treatment2011In: Graphene 2011 - 11th to 14th April 2011. Bilbao, Spain., 2011Conference paper (Refereed)
  • 6.
    Bohl Kullberg, Erika
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Bergstrand, Nill
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical Chemistry.
    Carlsson, Jörgen
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Edwards, Katarina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical Chemistry.
    Johnsson, Markus
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical Chemistry.
    Sjöberg, Stefan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gedda, Lars
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Development of EGF-conjugated liposomes for targeted delivery of boronated DNA-binding agents2002In: Bioconjugate chemistry, ISSN 1043-1802, E-ISSN 1520-4812, Vol. 13, no 4, p. 737-743Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Evidence for (π-allyl)palladium(II)(quinone) complexes in the palladium-catalyzed 1,4-diacetoxylation of conjugated dienes1988In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 29, no 18, p. 2243-2246Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Palladium‑Hydroquinone Catalysed Electrochemical 1,4‑Oxidation of Conjugated Dienes1987In: Journal of the Chemical Society. Chemical communications, ISSN 0022-4936, Vol. 16, p. 1236-1238Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Bohman, Ove
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Pettersson, L. G. M.
    UNIV STOCKHOLM, DEPT THEORET PHYS, S-11346 STOCKHOLM, SWEDEN.
    Siegbahn, Hans O. G.
    Uppsala University, Disciplinary Domain of Science and Technology, Physics.
    Electronic Structure of Catalytically Important Palladium Complexes Studied by Photoelectron Spectroscopy1992In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 11, no 5, p. 1784-1788Article in journal (Refereed)
  • 10.
    Church, Tamara L.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Rasmussen, Torben
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Enantioselectivity in the Iridium-Catalyzed Hydrogenation of Unfunctionalized Olefins2010In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 29, no 24, p. 6769-6781Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Catalytic asymmetric chiral lithium amide-promoted epoxide rearrangement: a NMR spectroscopic and kinetic investigation2010In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 21, no 21-22, p. 2733-2739Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry 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‑ones1991In: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 29, no 1, p. 54-62Article in journal (Refereed)
    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 University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Rapid microwave-assisted solid phase peptide synthesis2002In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 11, p. 1592-1596Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Imaging of Enzymes in the Steroid Biosynthetic Pathway: Synthesis of 18F-Labelled Tracers2009Doctoral thesis, comprehensive summary (Other academic)
    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.

    List of papers
    1. Synthesis of 11C-labelled metomidate analogues as adrenocortical imaging agents
    Open this publication in new window or tab >>Synthesis of 11C-labelled metomidate analogues as adrenocortical imaging agents
    2008 (English)In: J. Label Compd Radiopharm, no 51, p. 273-276Article in journal (Refereed) Published
    National Category
    Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-16689 (URN)doi:10.1002/jlcr.1517 (DOI)
    Available from: 2008-06-24 Created: 2008-06-24 Last updated: 2011-01-11
    2. 18F-Labelled Metomidate Analogues as Adrenocortical Imaging Agents
    Open this publication in new window or tab >>18F-Labelled Metomidate Analogues as Adrenocortical Imaging Agents
    2009 (English)In: Nuclear Medicine and Biology, ISSN 0969-8051, E-ISSN 1872-9614, Vol. 36, no 4, p. 435-445Article in journal (Refereed) 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.

    Keywords
    n. c. a. nucleophilic 18F-fluorination, [18F]alkyl MTO analogues, adrenocortical tumours
    National Category
    Chemical Sciences
    Research subject
    Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-89065 (URN)10.1016/j.nucmedbio.2009.01.014 (DOI)000266146700013 ()19423012 (PubMedID)
    Available from: 2009-02-06 Created: 2009-02-06 Last updated: 2017-12-14Bibliographically approved
    3. Synthesis and in vitro evaluation of 18F-labelled di- and tri(ethylene glycol) metomidate esters
    Open this publication in new window or tab >>Synthesis and in vitro evaluation of 18F-labelled di- and tri(ethylene glycol) metomidate esters
    2009 (English)In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 52, no 7-8, p. 278-285Article in journal (Refereed) 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.

     

    Keywords
    n.c.a. nucleophilic 18F-fluorination, di- and tri(ethylene glycol), metomidate, analogues
    National Category
    Chemical Sciences
    Identifiers
    urn:nbn:se:uu:diva-88794 (URN)10.1002/jlcr.1597 (DOI)000268690300029 ()
    Available from: 2009-02-06 Created: 2009-02-06 Last updated: 2017-12-14Bibliographically approved
    4. 18F-Labelled vorozole analogues as PET tracer for aromatase
    Open this publication in new window or tab >>18F-Labelled vorozole analogues as PET tracer for aromatase
    2008 (English)In: J. Label Compd Radiopharm, no 51, p. 207-212Article in journal (Refereed) Published
    Keywords
    n. c. a. nucleophilic 18f-fluorination, 18F-labelled VOZ nalaogues, aromatase
    National Category
    Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-16607 (URN)doi:10.1002/jlcr.1502 (DOI)
    Available from: 2008-05-29 Created: 2008-05-29 Last updated: 2011-01-11
    5. Pharmacological characterization of 18F-labeled vorozole analogues.
    Open this publication in new window or tab >>Pharmacological characterization of 18F-labeled vorozole analogues.
    Show others...
    (English)Manuscript (Other academic)
    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.

    Keywords
    aromatase, autoradiography, biodistribution, PET, rat brain, vorozole
    National Category
    Other Basic Medicine Medical and Health Sciences
    Research subject
    Organic Chemistry; Medicine
    Identifiers
    urn:nbn:se:uu:diva-88793 (URN)
    Available from: 2009-02-06 Created: 2009-02-06 Last updated: 2018-01-13
    6. Automated synthesis of 18F-labelled analogues of etomidate, vorozole and harmine using commercial synthesizer TRACERLab FXFN
    Open this publication in new window or tab >>Automated synthesis of 18F-labelled analogues of etomidate, vorozole and harmine using commercial synthesizer TRACERLab FXFN
    (English)Manuscript (Other academic)
    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.       

    Keywords
    PET, TRACERLab FXFN, ETO, VOZ, HAR, automation
    National Category
    Other Basic Medicine Organic Chemistry
    Research subject
    Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-88789 (URN)
    Available from: 2009-02-06 Created: 2009-02-06 Last updated: 2018-01-13
  • 15.
    Garg, Neeraj
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Westerlund, C
    Sundell, S
    Karlen, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    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 rearrangement1996In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 52, no 48, p. 15209-15224Article in journal (Refereed)
    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 University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sköld, Christian
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Plouffe, Bianca
    Lindeberg, Gunnar
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Botros, Milad
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences, Biological Research on Drug Dependence.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Nyberg, Fred
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences, Biological Research on Drug Dependence.
    Gallo-Payet, Nicole
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Karlén, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Angiotensin II Pseudopeptides Containing 1,3,5-Trisubstituted Benzene Scaffolds with High AT2 Receptor Affinity2005In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 48, no 21, p. 6620-6631Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Structural Assignment of  σ-π-Palladium Complexes by 2D NMR1993In: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 31, no 10, p. 954-959Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Axen, Andreas
    Uppsala University.
    (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)-pal1997In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 16, no 6, p. 1167-1178p. 1167-1178Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    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-Oxopurine1993In: Heterocycles, ISSN 0385-5414, E-ISSN 1881-0942, Vol. 36, no 2, p. 231-235Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Plobeck, Niklas A.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Comparison of one- and two-dimensional techniques in the unambiguous 13C NMR spectral assignment of ellipticine and related indole derivatives1990In: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 28, p. 635-641Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Tanner, David
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Complete 1H and 13C NMR spectral assignment of venturicidin A by 2D NMR spectroscopy1989In: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 27, no 9, p. 863-871Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Örnebro, Jörgen
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Bäckvall, Jan-Erling
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Mechanism of Apparent π-Allyl Rotation in (π-Allyl)Palladium Complexes with Bidentate Nitrogen Ligands1994In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 116, no 8, p. 3631-3632Article in journal (Refereed)
  • 23.
    Grennberg, Helena
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Bäckvall, Jan-Erling
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Acid‑Induced Transformation of Palladium(0)­‑Benzoquinone Complexes to Palladium(II) and Hydroquinone1993In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 12, no 5, p. 1790-1793Article in journal (Refereed)
  • 24.
    Grennberg, Helena
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Bäckvall, Jan-Erling
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Use of Sulfoxides as Co‑catalysts in the Palladium‑Quinone‑Catalyzed 1,4‑Diacetoxylation of 1,3‑Dienes: An Example of Ligand‑Accelerated Catalysis1991In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 56, no 20, p. 5811-5811Article in journal (Refereed)
  • 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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Undheim, Kjell
    UNIV OSLO, DEPT CHEM, POB 1033, N-0315 OSLO, NORWAY.
    Regiochemistry and Stereochemistry in Pd(0)‑Catalyzed Allylic Alkylation of Nucleoside Bases1992In: Acta Chemica Scandinavica, ISSN 0904-213X, E-ISSN 1902-3103, Vol. 46, p. 761-771Article in journal (Refereed)
  • 26.
    Helander, Anders
    et al.
    Uppsala University, Department of Zoophysiology.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Mechanisms for Plasma‑Mediated Activation of Human Blood Cell Aldehyde Dehydrogenase1992In: Biochimica et Biophysica Acta. Molecular Cell Research, ISSN 0167-4889, E-ISSN 1879-2596, Vol. 1136, no 3, p. 259-264Article in journal (Refereed)
    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 University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Karlsson, John
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Enzymatic Kinetic Resolution of 1-(3-furyl)-3-buten-1ol2005In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 16, p. 2397-2399Article in journal (Other academic)
    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 University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Experimental Physics.
    Blom, Tobias
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Experimental Physics.
    Widenqvist, Erika
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Materials Chemistry, Inorganic Chemistry.
    Carva, Karel
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Materials Theory.
    Sanyal, Biplab
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Materials Theory.
    Eriksson, Olle
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Materials Theory.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Jansson, Ulf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Materials Chemistry, Inorganic Chemistry.
    Quinlan, R.A.
    College of William and Mary, US.
    Holloway, B.
    Luna Innovations Incorporated.
    Surpi, Alessandro
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Experimental Physics.
    Leifer, Klaus
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Experimental Physics.
    Control of Conductivity in Graphene by Formation of Defects2008In: AVS 55th International Symposium & Exhibition 2008, October 19-24, Boston, USA, 2008Conference paper (Refereed)
    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 University.
    Lindeberg, G
    Uppsala University.
    Tong, WM
    Uppsala University.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Synnergren, B
    Uppsala University.
    Nyberg, F
    Uppsala University.
    Karlen, A
    Uppsala University.
    Hallberg, A
    Uppsala University.
    Angiotensin II analogues encompassing 5,9-and 5,10-fused thiabicycloalkane tripeptide mimetics1999In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 42, no 22, p. 4524-4537p. 4524-4537Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Lindeberg, Gunnar
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Johansson, Anja
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Nikiforovich, Gregory V
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Synnergren, Barbro
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences.
    Le Greves, Madeleine
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences.
    Nyberg, Fred
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences, Biological Research on Drug Dependence.
    Karlen, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Vinyl sulfide cyclized analogues of angiotensin II with high affinity and full agonist activity at the AT(1) receptor2002In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 45, no 9, p. 1767-1777Article in journal (Refereed)
    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 University.
    Dunn, Victoria
    Uppsala University.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Langer, Vratislav
    Uppsala University.
    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 lactones1999In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 64, no 1, p. 101-119p. 101-119Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Pour, Milan
    CZECHOSLOVAK ACAD SCI, INST ORGAN CHEM & BIOCHEM, CS-16610 PRAGUE 6, CZECH REPUBLIC.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry 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‑ol1990In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 112, no 18, p. 6735-6737Article in journal (Refereed)
  • 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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Corner Opening of Cyclopropane by Mercury(II) and Thallium(III) and Transmetallation of the Intermediate Organomercurials: A  Novel, Stereoselective Approach to Cyclobutanes and Cyclopropanes1994In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 116, no 1, p. 186-197Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    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 Reaction1992In: Journal of the Chemical Society, Chemical Communications, ISSN 0022-4936, Vol. 15, p. 1086-1087Article in journal (Refereed)
    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 University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Schmidt, Boris
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Fmoc protected peptide mimetic based on a cyclohexane framework and incorporation into angiotensin II1997In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 53, no 37, p. 12497-12504Article in journal (Refereed)
    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 University, Medicinska vetenskapsområdet, Faculty of Medicine, Department of Neuroscience. Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Nilsson, A
    Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Hagberg, G
    Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Langstrom, B
    Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Bergstrom, M
    Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    PET with 11C-deuterium-deprenyl and 18F-FDG in focal epilepsy2001In: Acta Neurologica Scandinavica, Vol. 103, p. 360-Article in journal (Refereed)
  • 37.
    Lindman, Susanna
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Lindeberg, Gunnar
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Nyberg, Fred
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences, Biological Research on Drug Dependence.
    Karlen, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Synthesis, receptor binding affinities and conformational properties of cyclic methylenedithioether analogues of angiotensin II2001In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 9, no 3, p. 763-772Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    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 Analysis1993In: Phosphorus Sulfur and Silicon and the Related Elements, ISSN 1042-6507, E-ISSN 1563-5325, Vol. 74, p. 429-430Article in journal (Refereed)
  • 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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Azinylsulfides. Part XV. X‑Ray Structure and NMR Assignment of 3,4‑Dimethylthioquinoline1991In: Journal of crystallographic and spectroscopic research, ISSN 0277-8068, Vol. 21, no 5, p. 559-565Article in journal (Refereed)
    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 University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry. Department of Physical and Analytical Chemistry, Quantum Chemistry.
    Frändberg, Åke
    Hedlund, Monica
    Lunell, Sten
    Physics, Department of Quantum Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry. Department of Physical and Analytical Chemistry, Quantum Chemistry.
    Sedin, Gunnar
    LIBENS MERITO - Festskrift till Stig Strömholm på sjuttioårsdagen 16 september 20012001Book (Other scientific)
  • 41. Mazuela, Javier
    et al.
    Norrby, Per-Ola
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    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 Study2011In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 133, no 34, p. 13634-13645Article in journal (Refereed)
    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 University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Pamies, Oscar
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Dieguez, Montserrat
    Phosphite-oxazole/imidazole ligands in asymmetric intermolecular Heck reaction2011In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 9, no 3, p. 941-946Article in journal (Refereed)
    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.