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  • 1.
    Ahlgren, Joakim
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry.
    De Brabandere, Heidi
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry.
    Reitzel, Kasper
    Rydin, Emil
    Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Evolution. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Genetics, Limnology.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Waldebäck, Monica
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry.
    Sediment Phosphorus Extractants for Phosphorus-31 Nuclear Magnetic Resonance Analysis: A Quantitative Evaluation2007In: Journal of Environmental Quality, ISSN 0047-2425, E-ISSN 1537-2537, Vol. 36, no 3, p. 892-898Article in journal (Refereed)
    Abstract [en]

    The influence of pre-extractant, extractant, and post-extractant on total extracted amounts of P and organic P compound groups measured with 31P nuclear magnetic resonance (31P-NMR) in lacustrine sediment was examined. The main extractants investigated were sodium hydroxide (NaOH) and sodium hydroxide ethylenediaminetetraacetic acid (NaOH-EDTA) with bicarbonate buffered dithionite (BD) or EDTA as pre-extractants. Post extractions were conducted using either NaOH or NaOH-EDTA, depending on the main extractant. Results showed that the most efficient combination of extractants for total P yield was NaOH with EDTA as pre-extractant, yielding almost 50% more than the second best procedure. The P compound groups varying the most between the different extraction procedures were polyphosphates and pyrophosphates. NaOH with BD as pre-extractant was the most efficient combination for these compound groups.

  • 2.
    Ahlgren, Joakim
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Faculty of Science and Technology, Biology, Department of Ecology and Evolution, Limnology. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Physical and Analytical Chemistry.
    Reitzel, Kasper
    Danielsson, Rolf
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Faculty of Science and Technology, Biology, Department of Ecology and Evolution, Limnology. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Physical and Analytical Chemistry.
    Gogoll, Adolf
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Faculty of Science and Technology, Biology, Department of Ecology and Evolution, Limnology.
    Rydin, Emil
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Faculty of Science and Technology, Biology, Department of Ecology and Evolution, Limnology.
    Biogenic phosphorus in oligotropic mountain lake sediments: Differences in composition measured with NMR spectroscopy2006In: Water Research, no 40, p. 3705-3712Article in journal (Refereed)
  • 3.
    Ahlgren, Joakim
    et al.
    Institute of Biology, University of Southern Denmark, Campusvej 55, DK-5230 Odense M, Denmark.
    Reitzel, Kasper
    Institute of Biology, University of Southern Denmark, Campusvej 55, DK-5230 Odense M, Denmark.
    De Brabandere, Heidi
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Rydin, Emil
    Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Genetics, Limnology.
    Release of Organic P Forms from Lake Sediments2011In: Water Research, ISSN 0043-1354, E-ISSN 1879-2448, Vol. 45, no 2, p. 565-572Article in journal (Refereed)
    Abstract [en]

    The effects of different physical and chemical conditions on the decomposition and release of organic and inorganic P compound groups from the sediment of Lake Erken were investigated in a series of laboratory experiments. Conditions investigated were temperature, oxygen level, and the effects of additions of carbon substrate (glucose) and poison (formalin). The effects on the P compound groups were determined by measurements with 31P NMR before and after the experiments, as well as analysis of P in effluent water throughout the experiment. Phosphate analysis of the effluent water showed that oxygen level was the most influential in terms of release rates, with the sediments under anoxic conditions generally releasing more phosphate than the other treatments. 31P NMR showed that the various treatments did influence the P compound group composition of the sediment. In particular, the addition of glucose led to a decrease in orthophosphate and polyphosphate while the addition of formalin led to a decrease in phosphorus lipids, DNAphosphate and polyphosphate. Oxic conditions resulted in an increase in polyphosphates, and anoxic conditions in a decrease in these. Temperature did not seem to affect the composition significantly.

  • 4.
    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.

  • 5.
    Ahlgren, Joakim
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Analytical Chemistry.
    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 I.
    Waldebäck, Monica
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Analytical Chemistry.
    Markides, Karin
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Analytical Chemistry.
    Rydin, Emil
    Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Evolution, Limnology.
    Sediment Depth Attenuation of Biogenic Phosphorus Compounds Measured by 31P NMR2005In: Environmental Science and Technology, ISSN 0013-936X, E-ISSN 1520-5851, Vol. 39, no 3, p. 867-872Article in journal (Refereed)
    Abstract [en]

    Being a major cause of eutrophication and subsequent loss of water quality, the turnover of phosphorus (P) in lake sediments is in need of deeper understanding. A major part of the flux of P to eutrophic lake sediments is organically bound or of biogenic origin. This P is incorporated in a poorly described mixture of autochthonous and allochthonous sediment and forms the primary storage of P available for recycling to the water column, thus regulating lake trophic status. To identify and quantify biogenic sediment P and assess its lability, we analyzed sediment cores from Lake Erken, Sweden, using traditional P fractionation, and in parallel, NaOH extracts were analyzed using 31P NMR. The surface sediments contain orthophosphates (ortho-P) and pyrophosphates (pyro-P), as well as phosphate mono- and diesters. The first group of compounds to disappear with increased sediment depth is pyrophosphate, followed by a steady decline of the different ester compounds. Estimated half-life times of these compound groups are about 10 yr for pyrophosphate and 2 decades for mono- and diesters. Probably, these compounds will be mineralized to ortho-P and is thus potentially available for recycling to the water column, supporting further growth of phytoplankton. In conclusion, 31P NMR is a useful tool to asses the bioavailability of certain P compound groups, and the combination with traditional fractionation techniques makes quantification possible.

  • 6.
    Aune, Marie
    et al.
    Uppsala University.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Matsson, Olle
    Uppsala University.
    Solvent Dependence of Enantioselectivity for a Base Catalyzed 1,3-Hydron Transfer Reaction: A Kinetic Isotope Effect and NMR Spectroscopic Study.1995In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 60, no 5, p. 1356-1364p. 1356-1364Article in journal (Refereed)
    Abstract [en]

    The base-catalyzed rearrangement of 1-methylindene (1) to 3-methylindene (2) has been studied. The reaction proceeds with substrate enantioselectivity (kinetic resolution) when chiral tertiary amines are used as catalysts. When dihydroquinidine (DHQD) (3

  • 7.
    Axen, A
    et al.
    Uppsala University.
    Grennberg, H
    Uppsala University.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    One-pot synthesis of a 1,3,7,9-tetraazacyclododecane derivative and an investigation of its complexation properties1998In: Journal of Chemical Research, Synopses, no 11, p. 712-713p. 712-713Article in journal (Refereed)
    Abstract [en]

    A one-pot synthesis of a 1,3,7,9-tetraazacyclododecane macrocycle in 37% yield from inexpensive starting materials is described, and its complexation properties with metal cations are investigated.

  • 8.
    Bergman, Jan
    et al.
    CNT, DEPT ORGAN CHEM, S-14157 HUDDINGE, SWEDEN .
    Lidgren, Göran
    ROYAL INST TECHNOL, DEPT ORGAN CHEM, S-10044 STOCKHOLM 70, SWEDEN.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Synthesis and Reactions of Oxazolones from L‑Tryptophan and α‑Haloacetic Anhydrides1992In: Bulletin des Sociétés chimiques belges, ISSN 0037-9646, Vol. 101, no 7, p. 643-660Article in journal (Refereed)
    Abstract [en]

    Optically active 5(4H)-oxazolones have been synthesized from L-tryptophan and an excess of trifluoro-, trichloro-, and dichloroacetic anhydrides. Some of the 5(4H)-xazolones have been further transformed to the isomeric 5(2H)-oxazolones as well as oxazolones with exocyclic double bonds. Treatment of the various oxazolones under hydrolytic, acidic and Friedel-Crafts acylation conditions gave indole-3-pyruvic acid, alpha,beta-dehydrotryptophans, beta-carbolines as well as the functionalized cyclopentanoindole 32. Treatment of the 4-(3-indolylmethyl)-2-trifluoromethyl-5(2H)-oxazolone (17) with trifluoroacetic acid gave the 3,4-bridged azepinoindole 35.

  • 9.
    Bergman, Jan
    et al.
    Department of Organic Chemistry, CNT, Novum Research Park, S-141 52 Huddinge Sweden.
    Venemalm, Lennart
    Department of Organic Chemistry, Royal Institute of Technology, 8-100 44 Stockholm Sweden.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Synthesis of cyclopent[b]indolones1990In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 46, no 17, p. 6067-6084Article in journal (Refereed)
    Abstract [en]

    A number of cyclopent[b]indol-1-ones as well as -3-ones have been synthesized, using a new methodology involving intramolecular ring closure of α,β-unsaturated acylindoles. In some cases 1,2,3,4-tetrahydrocarbazol-4-ones were obtained. This methodology was used in the syntheses of the indole alkaloid yuehchukene and the carbazole alkaloid analogue demethoxycarbazomycin B.

  • 10.
    Berner, Simon
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics.
    Biela, Sarah
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics.
    Ledung, Greger
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Bäckvall, Jan-E.
    Puglia, Carla
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics.
    Oscarsson, Sven
    Activity boost of a biomimetic oxidation catalyst by immobilization onto a gold surface2006In: Journal of Catalysis, ISSN 0021-9517, E-ISSN 1090-2694, Vol. 244, no 1, p. 86-91Article in journal (Refereed)
    Abstract [en]

    Thiol-functionalized cobalt porphyrins were used as a model system for investigating catalytic activity in homogeneous and heterogeneous oxidation catalysis. Self-assemble monolayers of thiol-functionalized cobalt porphyrins were prepared on a gold surface and served as heterogenous catalysts. These immoblilized molecules prevented the strong inactivation observed for their homogeneous congener. As a result, the turnover number per molecule in heterogeneous catalysis was at least 100 times higher than that of the corresponding homogeneous catalyst. It is atypical for a heterogenized catalyst to outperform its homogeneous congener. The properties of the molecular layers were characterized on the molecular level by means of X-ray photoelectorn spectroscopy (XPS) and scanning tunneling microscopy (STM). The results demonstrate that the performance of these biomimetic catalysts can be dramatically improved if the catalyst arangement can be controlled on the molecular level.

  • 11.
    Blom, Magnus
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Huang, Hao
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Photoswitchable peptidomimetics with a stiff-stilbene chromophore for inhibition of Mycobacterium tuberculosis RNRManuscript (preprint) (Other academic)
    Abstract [en]

    Peptidomimetics incorporating two amino acids 1 and 2 with a stiff stilbene chromophore have been screened by a computational study and compared to a previously investigated analog 3 with stilbene chromophore. The effect of E-Z isomerization of the chromophores on the conformational properties of the petidomimetics was assessed via the frequency of hydrogen bonding between the two peptide strands attached to either side of the chromophore. Substantial differences between the three amino acids were thus indicated, in line with the anticipated effect of chromophore rigidity variation.

  • 12.
    Blom, Magnus
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Huang, Hao
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Synthesis and characterization of photoswitchable stiff-stilbene based amino acid derivativesManuscript (preprint) (Other academic)
    Abstract [en]

    Synthetic routes towards the Boc-protected amino acids 1 and 2 incorporating the stiff stilbene chromophore via the corresponding indanone carboxylic acids have been devised. Crucial steps are a reductive McMurry coupling of the indanone carboxylic acids, yielding stiff stilbene dicarboxylic acid esters. Hydrolysis to the monoester and conversion to the azides, followed by a Curtius rearrangement afforded the Boc-protected amino acid ester 1.

  • 13.
    Blom, Magnus
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Norrehed, Sara
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Andersson, Claes-Henrik
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Huang, Hao
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Light, Mark E.
    Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K.
    Bergquist, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Analytical Chemistry.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis2016In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 21, no 1Article in journal (Refereed)
    Abstract [en]

    Abstract: Ditopic binding of various dinitrogen compounds to three bisporphyrin molecular tweezers with spacers of varying conformational rigidity, incorporating the planar ene-diyne (1), the helical stiff stilbene (2), or the semirigid glycoluril motif fused to  the porphyrins (3) are compared. Binding constants Ka = 10^4 to 10^6 M^-1 reveal subtle  differences between these tweezers, that are discussed in terms of porphyrin dislocation  modes. Exciton coupled circular dichroism (ECCD) of complexes with chiral dinitrogen  guests provides experimental evidence for the conformational properties of the tweezers. The results are further supported and rationalized by conformational analysis.

  • 14.
    Blom, Magnus
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Olsson, Sandra
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Norrehed, Sara
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Andersson, Claes-Henrik
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Photomodulable bis-porphyrin molecular tweezers as dynamic host systems for diamine guestsManuscript (preprint) (Other academic)
    Abstract [en]

    Bisporphyrin molecular tweezers with an enediyne (1) or a stiff stilbene (2) photoswitchable spacer are proposed as systems for modulation of bitopic binding to diamine guests via E/Z photoisomerization. The photoisomerization has been monitored by UV-Vis and 1H NMR spectroscopy and occurs without side reactions such as Bergman cyclization. Possible applications are rationalized in terms of competitive binding involving monoamine/diamine mixtures, and are supported by conformational analysis of the envisioned host-guest complexes. Binding dynamics for conformationally flexible guests show significantly different performance of aliphatic 1,w-diamine guests with varying N-N distance.

  • 15.
    Bäckvall, Jan-E.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Granberg, Kennth L.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Gatti, Roberto
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Stereocontrolled Lactonization Reactions via Palladium-Catalyzed 1,4-Addittion to Conjugated Dienes1993In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 58, no 20, p. 5445-5451Article in journal (Refereed)
    Abstract [en]

    Stereocontrolledp alladium(I1)-catalyzed1 ,4-chloro-and 1,4-acetoxylactonizations o f conjugated cyclic dienes have been developed to give stereodefined fused lactones. The stereochemistry of the 1,4- acetoxylactonization was controlled by the ligand on the metal catalyst, and in this way either a cisor truns-acetoxylactonization was obtained. This dual stereoselectivity is explained by a stereocontrolled acetate attack (trans or cis, respectively) on the allyl group in the catalytic (π-allyl)- palladium intermediate. To further strengthen the mechanism the intermediate (π-ally1)palladium complex was isolated and fully characterized. A stereospecific synthesis of cis-  and truns-2-[6- (benzyloxy)-2,4-heptadien-l-yllacetic a cid (cis-  and truns-9) followed by stereoselective Pd(I1)- catalyzed chloro- and acetoxylactonization in acetonelacetic acid resulted in highly functionalized fused lactones with control of the relative stereochemistry at four different carbons.

  • 16.
    Bäckvall, Jan-Erling
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Stone, Guy
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Syntheses of (±)-α- and (±)- γ- Lycorane via a Stereocontrolled Organopalladium Route1991In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 56, no 9, p. 2988-2993Article in journal (Refereed)
    Abstract [en]

    Total syntheses of (+/-)-alpha-and (+/-)-gamma-lycorane are described. The key steps in the syntheses are the stereocontrolled palladium-catalyzed intramolecular 1,4-chloroamidation of 12 to 13 and the subsequent anti-stereoselective copper-catalyzed S(N)2' reaction of allylic chloride 13 with [3,4-(methylenedioxy)phenyl]magnesium bromide to give 14. Hexahydroindole 14 has the required relative stereochemistry between carbons 3a, 7, and 7a for alpha-lycorane (1a) and was transformed to the latter via 15 and 16. The epimeric gamma-lycorane (2) was obtained by performing the Bischler-Napieralski cyclization on 14, which led to a highly stereoselective isomerization to give exclusively 17. Compound 17 was subsequently transformed to 2. The overall yield from ester 8 to (+/-)-alpha- and (+/-)-gamma-lycorane was 40 and 36%, respectively.

  • 17.
    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.

  • 18.
    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.

  • 19.
    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)
  • 20.
    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.

  • 21.
    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.

  • 22.
    Erdélyi, M
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Langer, V
    Karlén, A
    Gogoll, Adolf
    Insight into B-Hairpin Stability: A Structural and Thermodynamic Study of Diastereomeric B-Hairpin Mimetics2002In: New J. Chem., no 26, p. 834-Article in journal (Other academic)
  • 23.
    Erdélyi, Máté
    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 I.
    Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating2001In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 12, p. 4165-4169Article in journal (Refereed)
    Abstract [en]

    A microwave-enhanced, rapid and efficient homogeneous-phase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides, bromides, triflates, and aryl chloride, as well as pyridine and thiophene derivatives with trimethylsilylacetylene. Excellent yields (80−95%) for substrates containing a large variety of substituents in different positions are obtained in 5−25 min.

  • 24.
    Erdélyi, Máté
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Rapid Microwave Promoted Sonogashira Coupling Reactions on Solid Phase2003In: Journal of Organic Chemistry, Vol. 68, no 16, p. 6431-6434Article in journal (Refereed)
    Abstract [en]

    A microwave-enhanced, rapid, and efficient solidphase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides and bromides with various acetylene derivatives giving excellent yields in 15 to 25 min. The scopes of homogeneous, solventless, and solid-phase conditions for Sonogashira coupling of aryl halides are compared.

  • 25.
    Erdélyi, Máté
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Langer, Vratislav
    Department of Environmental Inorganic Chemistry, Chalmers University of Technology.
    Karlén, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Gogoll, Adolf
    Insight into beta-hairpin stability: a structural and thermodynamic study of diastereomeric beta-hairpin mimetics2002In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 26, p. 834-843Article in journal (Refereed)
    Abstract [en]

    Two diastereomers of a model β-hairpin peptide mimetic were synthesized and studied with a combination of experimental (NMR, X-ray, CD, MS, IR) and computational methods (Monte Carlo/molecular mechanics calculations). The secondary structure-stabilizing effects of hydrophobic interactions and hydrogen bonding were investigated. Comparison of the extent of folded hairpin population in non-competitive, polar aprotic, and polar protic solvents illustrates the critical role of intramolecular hydrogen bonding on hairpin stability. Investigation of 1H NMR melting curves of the diastereomeric compounds in a variety of solvents allowed an evaluation of the role of hydrophobic effects on secondary structure stabilization to be made.

  • 26.
    Ersmark, Karolina
    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 I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Nervall, Martin
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Gutiérrez-de-Terán, Hugo
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Hamelink, Elizabeth
    Janka, Linda K.
    Clemente, Jose C.
    Dunn, Ben M.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Samuelsson, Bertil
    Åqvist, Johan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Hallberg, Anders
    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 I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Macrocyclic inhibitors of the malarial aspartic proteases plasmepsin I, II, and IV2006In: Biorganic & Medicinal Chemistry, no 14, p. 2197-2208Article in journal (Refereed)
  • 27.
    Ezzaher, Salah
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Photochemistry and Molecular Science, Molecular Biomimetics.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Bruhn, Clemens
    Ott, Sascha
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Photochemistry and Molecular Science, Molecular Biomimetics.
    Directing protonation in [FeFe] hydrogenase active site models by modifications in their second coordination sphere2010In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 46, no 31, p. 5775-5777Article in journal (Refereed)
    Abstract [en]

    Subtle changes in the second coordination sphere of [Cl(2)bdtFe(2)-(CO)(4)(Ph2P-CH2-X-CH2-PPh2)] (bdt = benzene-1,2-dithiolate, X = NCH3, NCH2CF3, CH2) that do not influence the electronic character of the Fe-2 center can however direct protonation to three different sites: the N in the bis-phosphane, the Fe-Fe bond or the bdt-S.

  • 28.
    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.

  • 29.
    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.

  • 30.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Gomes, João
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Bergkvist, Magnus
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Configurational Assignment of Acyclic (π-Allyl)Palladium Complexes: Analytical Application of Chelating Nitrogen Ligands1995In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 14, no 3, p. 1354-1364p. 1354-1364Article in journal (Refereed)
    Abstract [en]

    A method for assignment of the relative stereochemistry in acyclic pi-allyl)palladium complexes by H-1 NMR H-H coupling constants has been developed. It is based on the introduction of nitrogen chelating ligands of the bipyridyl type into the complexes. The analytical suitability of several other types of nitrogen chelating ligands has also been investigated. A model for rationalization of the observed relation between stereochemistry and spectral parameters is proposed. Introduction of the chelating ligand also affects the syn,anti equilibrium of the complexes. Isomer ratios depend upon the relative stereochemistry of the side chain as well as on the chelating ligand.

  • 31.
    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.

  • 32.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Grennberg, Helena
    Uppsala University.
    Axen, A
    Uppsala University.
    Chemical shift assignment of geminal protons in 3,7-diazabicyclo [3.3.1]nonanes: An unexpected deviation from the axial/equatorial chemical shift order1997In: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 35, no 1, p. 13-20p. 13-20Article in journal (Refereed)
    Abstract [en]

    The chemical shift order of axial and equatorial methylene protons in 1,5-disubstituted 3,7-diazabicyclo [3.3.1]nonan-9-ones may be altered by substituents in the 1,5-positions, but the corresponding alcohols behave differently. Unambiguous signal assign

  • 33.
    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

  • 34.
    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.

  • 35.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Johansson, Charlotte
    Axen, Andreas
    Grennberg, Helena
    Determination of absolute configuration of (pi-allyl)palladium complexes by NMR spectroscopy and stereoselective complexation2001In: Chemistry-A European Journal, ISSN 0947-6539, Vol. 7, no 2, p. 396-403Article in journal (Refereed)
    Abstract [en]

    The chiral chelating ligand N,N'-bis(phenylethyl)bispidine (1) forms a rigid cavity which accommodates (rc-allyl)palladium species with high selectivity In the resulting complex, the absolute configuration of the re-allyl ligand can be determined by the d

  • 36.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Oscarsson, Sven
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Biochemistry.
    Reaction of pyridine derivatives with butyl glycidyl ether as a model system for glycidyl ether modified agarose: structural assignment by selective inept spectra1990In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 46, no 7, p. 2539-2548Article in journal (Refereed)
    Abstract [en]

    The reaction of 2-thio-pyridine N-oxide, 2-amino-, 2-hydroxy, 2-thio-, and 4-thiopyridine with butyl glycidyl ether was investigated as a model system for the functionalization of 2,3-epoxypropyl activated agarose. Unambiguous structural assignment of the products was provided by selective INEPT and nuclear Overhauser difference spectra. All reactions were shown to give only one of the possible regioisomers. Further conclusions regarding the structure of the agarose derivatives were drawn from IR spectra.

  • 37.
    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.

  • 38.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Polavarapu, Prasad
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Enhanced Silver Ion Binding to a Rigid Bisarene Molecular Cleft with Formation of Nonpolar Pleated Sheets through Non-Ionic Intermolecular Forces2007In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 46, no 13, p. 5271-5275Article in journal (Refereed)
    Abstract [en]

    Silver ion complexation to bisarene ligands is enhanced by providing a conformationally rigid molecular cleft in the (Z)-acenaphthylene dimer 1. NMR titrations were used to determine complexation constants K for a series of ligands in tetrahydrofuran solution, with K = 4.9 M-1 for the Z dimer 1 and 0.4 M-1 for the E dimer 2. Higher values of K were observed in CDCl3/CD3OD 9:1 with K = 38 M-1 for 1 and K = 4.1 M-1 for 2. In the solid state, isolated clusters of [1·(AgCF3SO3)2]2 form a novel, pleated-sheet motif based on non-ionic interactions between clusters.

  • 39.
    Gogoll, Adolf
    et al.
    UNIV MUNSTER, INST ORGAN CHEM, CORRENS STR 40, D-4400 MUNSTER, FED REP GER .
    Schäfer, Hans-Jürgen
    UNIV MUNSTER, INST ORGAN CHEM, CORRENS STR 40, D-4400 MUNSTER, FED REP GER .
    Photoreaktionen amphiphiler Benzophenon‑ und Myristinsäurederivate in Micellen und Doppelschichtmembranen1987In: Liebigs Annalen der Chemie, ISSN 0170-2041, p. 589-596Article in journal (Refereed)
  • 40.
    Gogoll, Adolf
    et al.
    UNIV MUNSTER, INST ORGAN CHEM, CORRENS STR 40, D-4400 MUNSTER, FED REP GER .
    Schäfer, Hans-Jürgen
    UNIV MUNSTER, INST ORGAN CHEM, CORRENS STR 40, D-4400 MUNSTER, FED REP GER .
    Synthese und Eigenschaften photoreaktiver, amphiphiler Benzophenonderivate1987In: Liebigs Annalen der Chemie, ISSN 0170-2041, p. 597-606Article in journal (Refereed)
  • 41.
    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.

  • 42.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Tegenfeldt, Jörgen
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Materials Chemistry, Inorganic Chemistry.
    Oscarsson, Sven
    UNIV UPPSALA, CTR BIOMED, INST BIOCHEM, S-75123 UPPSALA, SWEDEN .
    CP/MAS carbon-13 NMR spectroscopy of epoxypropyl-activated agarose functionalized with pyridine derivatives1991In: Macromolecules, ISSN 0024-9297, E-ISSN 1520-5835, Vol. 24, no 16, p. 4727-4728Article in journal (Refereed)
  • 43.
    Gogoll, Adolf
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Toom, Lauri
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Grennberg, Helena
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Ligand-Induced Formation of an Adamantanoid Hexanuclear (π-Allyl) PdII(μ3-Hydroxo) Cluster Stacked as Hydrogen-Bonded Double Strands2005In: Angew. Chem. Int. Ed., no 44, p. 2295-2300Article in journal (Refereed)
  • 44. Gogoll, Adolf
    et al.
    Toom, Lauri
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Grennberg, Helena
    Ligand-Induced Formation of an Adamantanoid Hexanuclear (π-Allyl)PdII(μ3-Hydroxo) Cluster Stacked as Hydrogen-Bonded Double Strands2005In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 44, no 30, p. 4729-4731Article in journal (Refereed)
  • 45.
    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)
  • 46.
    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)
  • 47.
    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)
  • 48.
    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)
  • 49.
    Hao, Huang
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Karlsson, Christoffer
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strømme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Sjödin, Martin
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Quinone Based Polypyrroles for Energy Storage Materials2015Conference paper (Refereed)
  • 50.
    Hao, Huang
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Karlsson, Christoffer
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strømme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Sjödin, Martin
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Quinone Functionalized Polypyrroles: Organic Materials for Energy Storage2015Conference paper (Refereed)
    Abstract [en]

    Quinones, which are naturally occurring redox active organic compounds,have been proposed as cathode materials in lithium ionbatteries for their high theoretical specific capacities and more environmentallyfriendly manufacturing compared to conventional inorganiccathode materials (see figure on the right). However,many of them suffer from poor kinetics as well as capacity lossdue to dissolution.¹ In our work, by attaching quinones as pendantmoieties onto conducting polmers, e.g. polypyrroles, we havecomposed conducting redox polymers, which are expected to decreaseproblems with resistance and dissolution while retainingcapacity and cyclability² (see figure on the left). A series of monomericcompounds incorporating pyrrole and quinone units weresynthesized and polymerized electrochemically. The resultingpolymers were studied by in-situ spectro-electrochemical techniquesas well as by EQCM to elucidate the redox chemistry ofthe quinone units as well as the kinetics ofpolymer redox performance.

123 1 - 50 of 135
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