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  • 1.
    Adbo, Karina
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Håkan S.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Ankarloo, Jonas
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Norell, M C
    Olofsson, Linus
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Svenson, Johan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Örtegren, U
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Enantioselective synthetic receptors for Tröger’s base1999In: Bioorganic Chemistry, Vol. 27, no 5, p. 363-371Article in journal (Refereed)
  • 2. Alonso, Diego
    et al.
    Bertilsson, Sophie
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Johnsson, Sandra
    Nordin, Sofia
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Södergren, Mikael
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    New Expedient Route to Both Enantiomers of Nonproteinogenic a-Amino Acid Derivatives from the Unsaturated 2-Aza-Bicyclo Moiety1999In: J. Org. Chem., no 64, p. 2276-2280Article in journal (Refereed)
  • 3. Alonso, Diego
    et al.
    Brandt, Peter
    Nordin, Sofia
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Ru(arene)(amino alcohol)-Catalyzed Transfer Hydrogenation of Ketones: Mechanism and Origin of Enantioselectivity1999In: J. Am. Chem. Soc., no 121, p. 9580-9588Article in journal (Refereed)
    Abstract
  • 4.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Piletsky, S A
    Koch-Schmidt, Ann-Christin
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Mosbach, K
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Influence of monomer-template ratio on selectivity and load capacity of molecularly imprinted polymers: indications of template self-association1999In: Journal of Chromatography A, Vol. 848, no 1-2, p. 39-49Article in journal (Refereed)
  • 5.
    Bertilsson, Sophie
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Tedenborg, Lars
    Alonso, Diego
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Chiral N, N' - and N,O-Bidentate Anionic Ligands. Preparation, Metal Complexation, and Evalution in the Asymmetric Aziridination of Olefins1999In: Organometallics, no 18, p. 1281-1286Article in journal (Refereed)
  • 6. Brandt, Peter
    et al.
    Hedberg, Christian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Lawonn, Klaus
    Pinho, Pedro
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    A Theoretical and Experimental Study of the Asymmetric Addition of Dialkylzinc to N-(Diphenylphosphinoyl)benzalimine1999In: Chem. Eur. J., no 5, p. 1692-1699Article in journal (Refereed)
    Abstract
  • 7.
    Buskas, Therese
    Stockholm University.
    Synthesis of lactosamine-containing carbohydrate structures and development for their easy assembly and conjugation1999Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis is based on four publications. The first chapter describes preparation of anomerically pure thioethyl-, thiophenyl-, and n-pentenyl 2-azido-2-deoxy glycosyl building blocks from easily accessible per-acetylated glycosamines.

    In the second part, acetylated, benzylated and non-protected n-pentenyl glycosides are used as substrates for preparing various spacer functionalities, which are obtained by means of radical elongations, oxidations and reductions.

    The syntheses of a trisaccharide,a-D-GlcpNAc-(1-->4)-b-D-Galp-(1-->4)-b-D-GlcpNAc, and fragments thereof, linked to a long lipophilic aglycon, are described in the third part. For the formation of theb-D-Galp-(1-->4)-D-GlcpNAc bond, several differently protected glucosamine acceptors were prepared and their reactivity towards a disaccharide donor evaluated.

    Finally, lactosamine derivatives were prepared by regioselective galactosylation and used as building blocks in the chemical synthesis of various oligosaccharides. The syntheses of polylactosamine di-, tri- and tetramers were achieved by regioselective glycosylation. Also spacer containing sulfated N-acetyllactosamine and Lewis x structures were synthesised.

  • 8.
    Johannesson, P
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Lindeberg, G
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Tong, W
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Gogoll, Adolf
    Synnergren, B
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences.
    Nyberg, F
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences.
    Karlen, A
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Hallberg, A
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Angiotensin II analogues encompassing 5,9- and 5,10-fusedthiazabicycloalkane tripeptide mimetics.1999In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 42, p. 4524-4537Article in journal (Refereed)
  • 9.
    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

  • 10.
    Johannesson, Petra
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Lindeberg, Gunnar
    Tong, Weimin
    Gogoll, Adolf
    Karlen, Anders
    Hallberg, Anders
    A flexible regioselective method for bicyclization of peptides.1999In: Peptides for the New Millennium, Proceedings of the American Peptide Symposium, 16th, Minneapolis, MN, United States, 1999, p. 153-154Conference paper (Other scientific)
  • 11.
    Kers, Annika
    Stockholm University.
    Towards synthesis of biologically important phosphate analogues: exploring H-phosphonate and C-phosphonate chemistry1999Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis is based on studies directed towards the development of methods for the preparation of phosphorus containing natural products, with the focus on C-phosphonate nucleic acid analogues.

    Mechanistic studies concerning formation of the phosphorus-carbon bond resulted in development of two efficient protocols for the synthesis of C-phosphonates from the corresponding H-phosphonate derivatives. These were applied, inter alia, to the synthesis of a novel type of nucleotide analogue containing the 4-pyridylphosphonate internucleotide bond. Also, synthesis of new nucleoside 5'-methylenephosphonate building blocks, suitable for incorporation into oligonucleotides or their conjugates, and a new method for the preparation of alkyl H-phosphonates, are discussed. Finally, mechanistic investigations related to C-phosphonates formation via N->C phosphorus migration in certain complexes of DBU with chlorophosphates, are presented.

  • 12.
    Kers, Inger
    Stockholm University.
    Nucleoside phosphoramidates and related compounds: development of synthetic methods based on H-phosphonate chemistry1999Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In this thesis, studies directed towards development of new synthetic methods for the preparation of nucleotide analogues of potential medical value as antisense, antigene or antiviral agents, are described.

    Two methods for synthesis of N3'->P5' and P3'->N5' phosphoramidate analogues with the nitrogen atom in bridging position of the internucleotide linkage was developed. Both of them make use of the readily available H-phosphonate monoesters as starting materials and permit the introduction of multiple modifications at the phosphorus center. In conjunction with these, a simple and efficient method for the preparation of nucleoside H-phosphonothioates, as a starting material for various phosphate analogues was also developed. As part of theses studies, base-induced disproportionation of aryl H-phosphonates was investigated.

    A new type of prodrugs for AZT, symmetrical phosphoramidates, have been synthesised as potential anti-retroviral agent.

  • 13.
    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

  • 14. Langstrom, B
    et al.
    Kihlberg, T
    Bergstrom, M
    Antoni, G
    Bjorkman, M
    Forngren, B H
    Forngren, T
    Hartvig, P
    Markides, K
    Yngve, U
    Ogren, M
    Compounds labelled with short-lived beta(+)-emitting radionuclides and some applications in life sciences. The importance of time as a parameter1999In: Acta Chemica Scandinavica, ISSN 0904-213X, E-ISSN 1902-3103, Vol. 53, no 9, p. 651-669Article in journal (Refereed)
    Abstract [en]

    Some examples of recent development of the synthesis of compounds labelled with short-lived beta(+)-emitting radionuclides will be discussed with an emphasis on the importance of time in selecting a synthetic strategy. Furthermore the use of such labelled compounds to monitor certain processes in areas within the held of analytical chemistry and in various applications in drug development will be presented.

  • 15.
    Lindström, Ulf M.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Somfai, Peter
    Microwave-assisted aminolysis of vinylepoxides1999In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 40, no 52, p. 9273-9276Article in journal (Refereed)
    Abstract [en]

    Di- and trisubstituted vinyl epoxides in NH4OH were subjected to microwave irradn. affording the corresponding vicinal amino alcs. in high yields. The reaction is stereospecific and highly regioselective for addn. at the allylic carbon. [on SciFinder(R)]

  • 16.
    Linnerborg, Malin
    Stockholm University.
    Structural elucidation of the O-antigen polysaccharides of five Escherichia coli strains1999Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The cell walls of bacteria are composed to a large extent of different polysaccharides. In order to understand and thereby, be able to utilise the physical, biological and immunological properties of polysaccharides, it is important to determine their structures. In the present thesis, structural investigations of the O-antigen polysaccharides from five strains of Escherichia coli, serogroups O138, O164, O167, O173 and O159, are described.

    Nuclear Magnetic Resonance (NMR) spectroscopy was the primary technique employed. Fast Atom Bombardment Mass Spectrometry (FAB-MS) and Electrospray Mass Spectrometry (ESI-MS) together with chemical degradations of the polysaccharides were also utilised.

    The possibilities, advantages and disadvantages of certain available methods for such studies are discussed.

  • 17.
    Pettersson, Ethel
    Stockholm University.
    Mechanism Studies of Catalytic RNA, and RNA and DNA Model Compounds1999Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis describes mechanism studies of transesterifications of phosphate esters. The aim of the studies concerns two fields. First, the catalytic mechanism that group I introns use in self-splicing. The focus was on metal ion coordinating groups at the catalytic site. Studies were performed on a (almost) full-length group I intron. A 2'-amino modification was introduced in the co-substrate and metal ion switch experiments were carried out. In the presence of magnesium ions the reaction rate decreased but introducing nitrogen preferring metal ions as for example manganese, this negative trend could be reversed. Further studies of the catalytic mechanism were performed on the same group I intron but converted to a ribozyme by deleting the substrate site. We introduced a 2'-amino group in the leaving group nucleoside, in a chemical synthesized substrate and metal ion switch experiments were carried out. At most we could study the cleavage reaction with two 2'-amino modifications at the catalytic site, in the co-substrate and in the substrate. In the presence of two 2'-amino modifications we obtained more than additive effects on the rate, in the presence of manganese ions. These experiments showed how one catalytic metal ion coordinated to the 2'-position in the co-substrate and a second one to the 2'-position in the leaving sugar nucleoside. An alternative model of the earlier proposed two metal ion mechanism used by group I introns, is presented.

    Five RNA model compounds, methyl furanosides with a 5-diphenyl phosphate group were synthesized. The metal ion promoted intramolecular cyclisation reaction, where the 3-hydroxyl attacks the 5-diphenyl phosphate was studied in the presence of different divalent metal ions. Two derivatives contained a 2-amino group and higher reaction rates were obtained in experiments with nitrogen preferring metal ions. These studies showed the effect of an adjacent position, on the hydroxy nucleophile, via coordination of a metal ion and also give data supporting the mechanism model for the catalytic RNA. The other field in this thesis concerns investigations on why ethylene oxide causes more DNA damages, than propylene oxide. To exclude that the intramolecular phosphate transesterification reaction was responsible for the observed differences, two dithymidine alkyl phosphates were synthesized and studied. Further, to see that the respective epoxide did not have different alkylation rates toward a phosphate center, the alkylation rate for the respective epoxide was studied. Neither of these events could be ascribed to be responsible for the earlier observations concerning ethylene oxide and propylene oxide.

  • 18. Piletsky, S A
    et al.
    Andersson, Håkan S.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Combined hydrophobic and electrostatic interaction based recognition in molecularly imprinted polymers1999In: Macromolecules, Vol. 32, p. 633-636Article in journal (Refereed)
  • 19. Piletsky, S A
    et al.
    Terpetschnig, E
    Andersson, Håkan S.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Wolfbeis, O S
    Application of non-specific fluorescent dyes for monitoring enantio-selective ligand-polymer binding in molecularly imprinted polymers1999In: Fresenius Journal of Analytical Chemistry, Vol. 364, p. 512-516Article in journal (Refereed)
  • 20.
    Pinho, Pedro
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    A novel synthesis of chiral cyclopentyl- and cyclohexyl-amines1999In: Chem. Commun., no 597-598Article in journal (Refereed)
  • 21.
    Remonen, Tommi
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Hellberg, Jonas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Slatt, Johnny
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ethylenedithio end-capped oligothiophenes (bEDTnT); dimer, trimer and tetramer.1999In: Synthetic metals, ISSN 0379-6779, E-ISSN 1879-3290, Vol. 101, no 1-3, p. 107-108Article in journal (Refereed)
    Abstract [en]

    Two new ethylenedithio substituted thiophenes (I; R = H, Br) have been synthesized. Starting from I (R = Br), oligomers II (n = 0, 1, 2) were synthesized. Their cyclic voltammetric behavior and electronic structure (by UV-Vis) have been recorded. Low oxidn. potentials and small differences between first and second oxidn. potential were found. In the UV-Vis spectra large red shifts compared to other end-capped oligomers were obsd. [on SciFinder(R)]

  • 22.
    Söderman, Peter
    Stockholm University.
    Synthesis of oligosaccharides for structural, conformational and molecular recognition investigations1999Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Carbohydrates are involved cell-cell interaction. Synthesis of small and medium sized oligosaccharides is important to gain more understanding about the their physical properties that are crucial for their action in molecular recognition events. The first paper describes the synthesis, structural and conformational analysis of four different trisaccharides. The second paper describes a stereospecific synthesis of methyl a-(4-2H)-cellobioside, applying a regioselective oxidation stereospecific reduction sequence. In the third paper investigation of 1,3-dibromo-5,5-dimethylhydantoin in regioselective oxidation of stannylene acetals of different monosaccharide diols is described. The fourth study describes the synthesis of three different trisaccharides related to Escherichia coli O35 and Salmonella arizona O62, where the selective oxidation of a hydroxymethyl group using TEMPO is the key step. The last work summarize the synthesis of a model hexasaccharide from the core region of a Haemonchus contortus glycoprotein. The key steps in this synthesis are regioselective glucosidation to form a trisaccharide core followed by trifucosylation and conversion of a b-glucoside to the corresponding b-mannoside.

  • 23. Tanner, David
    et al.
    Wyatt, Paul
    Johansson, Fredrik
    Bertilsson, Sophie
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Studies on a Chiral (N,P) Ligand Containing a C2 -Symmetric Aziridine Unit1999In: Acta Chemica Scandinavica, no 53, p. 263-269Article in journal (Refereed)
  • 24.
    Thibaudeau, Christophe
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Bioorganic Chemistry.
    Stereoelectronic effects in nucleosides and nucleotides1999Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis is based on 12 original publications from 1994-98. Intramolecular stereoelectronicforces (anomeric and gauche effects), beside intermolecular forces such as hydrogen bonding,base stacking, electrostatics and hydration, have been found to be responsible for the localstructural changes of DNA and RNA and their components. A detailed insight into the stereoelectronic forces has been obtained by a systematic pairwise comparison of the thermodynamics in various N- and C-nucleosides at several pDs, determined from pseudorotational analyses of 3JHH. This has allowed us to understand how the electronic character of various sugar substituents modulates the strengths of the stereoelectronic drive of the sugar conformation. Evidences have been put forward supporting that both the anomeric and gauche effects result from the appropriate orbital mixing rather than dipole-dipole interactions: the nucleobase-dependent anomeric effect results nO4'→Σ* C1'-N1/9 interaction, whereas the gauche effect originates from Σ→Σ* orbital mixing. It has been demonstrated that the modulations of the gauche and the anomeric effect are interrelated, and mutually influence each other, and the final outcome of the free-energy of the sugar conformational equilibrium is a result of this enthalpic interplay and of the entropy. The electronic character of the nucleobase at various pDs is transmitted to steer the sugar conformation in β-nucleosides owing to the modulation of the anomeric and gauche effects. The strength of the anomeric effect in α-nucleosides is reduced compared to β-counterparts owing to weaker overlap of O4' lonepairs with Σ* C1'N1/9. In C-nucleosides, the conformation of the sugar moiety is dictated by nO4' →Σ* C1'C5/9(sp2) interactions, which are reduced and enhanced at acidic and alkaline pDs. The strength of the nO4'→Σ* C1'-N1/9 anomeric effect in adenosine and guanosine and in their 2'-deoxy counterparts has been quantitated using 9-deazaadenosine as a reference point for the estimation of the counteracting steric effect of the nucleobase in the N-nucleosides. The interaction of 2'-OH with the vicinal phosphate results in a unique two-state (N,εt ) ↔ (S,ε-) equilibrium in 3'- ethylphosphate ribonucleotides whereas in 2'-deoxy counterparts no correlation between sugar and phosphate-backbone conformation could be detected.

    A quantitative Karplus-type equation for the translation of 3JHF into ΦHCCF has beenparametrized for the first time, taking into account effects of orientation and electronegativity of substituents and the influence of HCC and FCC bond angle changes. The application of this equation to pseudorotational analyses of 3JHF in combination with 3JHH has allowed to quantitatively describe the conformation of several antiviral and antitumour mono and difluoronucleosides.

  • 25.
    Wachtmeister, Johanna
    Stockholm University.
    Synthesis of Potential Inhibitors Against HIV1999Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis describes the syntheses of various potential inhibitors of HIV, e.g. some 3´-hydroxymethyl-substituted carbocyclic nucleoside analogues as reverse transcriptase inhibitors and some symmetry-based peptidomimetics as protease inhibitors.

    Enantiomerically pure (3S,4S)-bis-(hydroxymethyl)cyclopentanone ethylene glycol ketal was used in the syntheses of eight functionalized cyclopentanol intermediates. These were either condensed with 6-chloropurine bases using the Mitsunobu reaction or converted into the corresponding cyclopentylamines, on which the purine bases were built up.

    The influence of the central hydroxyl groups on the anti-viral activity of L-mannaric acid based HIV-1 protease inhibitors was investigated. L-Iditol was used as the chiral precursor in the synthesis of the inhibitors with inverted configuration at C-3 and C-4.

    All target compounds described in this thesis were evaluated for anti-viral activity against the human immunodeficiency virus.

1 - 25 of 25
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