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Proton magnetic resonance studies of 5,6-saturated thymidine derivatives produced by ionizing radiation. Conformational analysis of 6-hydroxylated diastereoisomers

Abstract

The conformational properties of ten 6-hydroxylated dihydrothymidine derivatives including the various diastereoisomers of 5,6-dihydroxy-5,6-dihydrothymidine, 6-hydroxy-5,6-dihydrothymidine and 5-bromo-6-hydroxy-5,6-dihydrothymidine have been studied by 250 MHz proton magnetic resonance in aqueous solutions. A close correlation has been established between the carbon-6 configuration and the osidic conformation. The increase in the amplitude of the puckering within the furanose ring compared to that of thymidine or 2'-deoxyuridine is more pronounced for the levortatory (6S) nucleosides than for the dextrorotatory (6R) diastereoisomers. The importance of the 2'endo conformer population decreases in the following order: (-)> (+)>thymidine. The absence of destabilizing effects on the g/sup +/ rotameric population about the C(4')-C(5') bond denotes the lack of any interaction between exocyclic hydroxymethyl group and the 6-hydroxyl function or the 2-keto group. The 5,6-saturated nucleosides adopt a preferential anti conformation. The comparison has been extended to syn nucleosides which show opposite trends in the sugar conformation and g/sup +/ distribution.
Authors:
Cadet, J; Ducolomb, R; [1]  Hruska, F E [2] 
  1. CEA Centre d'Etudes Nucleaires de Grenoble, 38 (France). Lab. de Radiobiologie
  2. Manitoba Univ., Winnipeg (Canada). Dept. of Chemistry
Publication Date:
Jun 20, 1979
Product Type:
Journal Article
Reference Number:
AIX-10-484094; EDB-80-041184
Resource Relation:
Journal Name: Biochim. Biophys. Acta - Nucl. Acids Protein Synth.; (Netherlands); Journal Volume: 563:1
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; THYMIDINE; MOLECULAR STRUCTURE; AQUEOUS SOLUTIONS; CHEMICAL RADIATION EFFECTS; ELECTRONIC STRUCTURE; IONIZING RADIATIONS; MAGNETIC RESONANCE; MHZ RANGE 100-1000; PROTONS; AZINES; BARYONS; CHEMISTRY; DISPERSIONS; ELEMENTARY PARTICLES; FERMIONS; FREQUENCY RANGE; HADRONS; HETEROCYCLIC COMPOUNDS; MHZ RANGE; MIXTURES; NUCLEONS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; PYRIMIDINES; RADIATION CHEMISTRY; RADIATION EFFECTS; RADIATIONS; RESONANCE; RIBOSIDES; SOLUTIONS; 400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)
OSTI ID:
5507967
Country of Origin:
Netherlands
Language:
English
Other Identifying Numbers:
Journal ID: CODEN: BBNPA
Submitting Site:
INIS
Size:
Pages: 206-215
Announcement Date:

Citation Formats

Cadet, J, Ducolomb, R, and Hruska, F E. Proton magnetic resonance studies of 5,6-saturated thymidine derivatives produced by ionizing radiation. Conformational analysis of 6-hydroxylated diastereoisomers. Netherlands: N. p., 1979. Web. doi:10.1016/0005-2787(79)90021-2.
Cadet, J, Ducolomb, R, & Hruska, F E. Proton magnetic resonance studies of 5,6-saturated thymidine derivatives produced by ionizing radiation. Conformational analysis of 6-hydroxylated diastereoisomers. Netherlands. doi:10.1016/0005-2787(79)90021-2.
Cadet, J, Ducolomb, R, and Hruska, F E. 1979. "Proton magnetic resonance studies of 5,6-saturated thymidine derivatives produced by ionizing radiation. Conformational analysis of 6-hydroxylated diastereoisomers." Netherlands. doi:10.1016/0005-2787(79)90021-2. https://www.osti.gov/servlets/purl/10.1016/0005-2787(79)90021-2.
@misc{etde_5507967,
title = {Proton magnetic resonance studies of 5,6-saturated thymidine derivatives produced by ionizing radiation. Conformational analysis of 6-hydroxylated diastereoisomers}
author = {Cadet, J, Ducolomb, R, and Hruska, F E}
abstractNote = {The conformational properties of ten 6-hydroxylated dihydrothymidine derivatives including the various diastereoisomers of 5,6-dihydroxy-5,6-dihydrothymidine, 6-hydroxy-5,6-dihydrothymidine and 5-bromo-6-hydroxy-5,6-dihydrothymidine have been studied by 250 MHz proton magnetic resonance in aqueous solutions. A close correlation has been established between the carbon-6 configuration and the osidic conformation. The increase in the amplitude of the puckering within the furanose ring compared to that of thymidine or 2'-deoxyuridine is more pronounced for the levortatory (6S) nucleosides than for the dextrorotatory (6R) diastereoisomers. The importance of the 2'endo conformer population decreases in the following order: (-)> (+)>thymidine. The absence of destabilizing effects on the g/sup +/ rotameric population about the C(4')-C(5') bond denotes the lack of any interaction between exocyclic hydroxymethyl group and the 6-hydroxyl function or the 2-keto group. The 5,6-saturated nucleosides adopt a preferential anti conformation. The comparison has been extended to syn nucleosides which show opposite trends in the sugar conformation and g/sup +/ distribution.}
doi = {10.1016/0005-2787(79)90021-2}
journal = {Biochim. Biophys. Acta - Nucl. Acids Protein Synth.; (Netherlands)}
volume = {563:1}
journal type = {AC}
place = {Netherlands}
year = {1979}
month = {Jun}
}