13C-31P couplings in the study of conformational properties of some diastereomeric nucleoside-3′-thiophosphate derivatives

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Abstract

Synthesis and stereochemical characterization of enantiomerically pure nucleoside-3́-phosphorothioate esters and salts are reported. Vicinal carbon phosphorus couplings reflect different predominance of the ε conformation in the isomeric (Rp and Sp) esters, while for the salts the εt conformation prevails in both stereoisomers. The influence of solvent and temperature on the conformational preferences is also described.

Original languageEnglish
Pages (from-to)247-257
Number of pages11
JournalNucleosides, Nucleotides and Nucleic Acids
Volume24
Issue number4
DOIs
Publication statusPublished - Jul 22 2005

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Keywords

  • C
  • H
  • Modified nucleotides
  • P NMR C-P coupling constants
  • Solution Conformation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Genetics

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