13C-31P couplings in the study of conformational properties of some diastereomeric nucleoside-3'-thiophosphate derivatives.
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.
Gács-Baitz
Eszter
E
Institute of Structural Chemistry, Chemical Research Center, Hungarian Academy of Sciences, Budapest, Hungary. egacs@chemres.hu
Sági
Gyula
G
Kajtár-Peredy
Mária
M
D002244:Carbon / Q000737:chemistry*; D002247:Carbon Isotopes / Q000737:chemistry; D002845:Chromatography; D004583:Electrons; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D013058:Mass Spectrometry; D008956:Models, Chemical; D008968:Molecular Conformation; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*; D010759:Phosphorus Isotopes / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D002247:Carbon Isotopes; D009705:Nucleosides; D010710:Phosphates; D010759:Phosphorus Isotopes; D010758:Phosphorus; D002244:Carbon; C035638:thiophosphoric acid