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

Eszter Gács-Baitz; Gyula Sági; Mária Kajtár-Peredy

doi:10.1081/NCN-59691

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

Nucleosides Nucleotides Nucleic Acids. 2005;24(4):247-57. doi: 10.1081/NCN-59691.

Authors

Eszter Gács-Baitz¹, Gyula Sági, Mária Kajtár-Peredy

Affiliation

¹ Institute of Structural Chemistry, Chemical Research Center, Hungarian Academy of Sciences, Budapest, Hungary. egacs@chemres.hu

PMID: 16021910
DOI: 10.1081/NCN-59691

Abstract

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

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbon / chemistry*
Carbon Isotopes / chemistry
Chromatography
Electrons
Magnetic Resonance Spectroscopy / methods*
Mass Spectrometry
Models, Chemical
Molecular Conformation
Nucleic Acid Conformation
Nucleosides / chemistry*
Phosphates / chemistry*
Phosphorus / chemistry*
Phosphorus Isotopes / chemistry
Stereoisomerism
Temperature

Substances

Carbon Isotopes
Nucleosides
Phosphates
Phosphorus Isotopes
Phosphorus
Carbon
thiophosphoric acid