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Solution structure of diastereomeric thymidine 3′‐O(N,N‐diisopropyl‐O‐β‐cyanoethyl‐phosphoramidothioate)s by NMR spectroscopy
Author(s) -
GácsBaitz Eszter,
KajtárPeredy Mária
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10144
Subject(s) - diastereomer , chemistry , vicinal , nuclear overhauser effect , nucleoside , nuclear magnetic resonance spectroscopy , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , spectroscopy , crystallography , organic chemistry , physics , quantum mechanics
The conformational properties of a diastereomeric nucleoside‐phosphorothioate pair is reported as reflected by different NMR parameters. Configurational assessment is based partly on the different NOE (nuclear overhauser enhancement) effects of the individual isomers and on the trends observed in other NMR parameters. Vicinal carbon‐phosphorus couplings reflect the predominance of the ϵ ‐ conformation for the Sp isomer and the ϵ t conformation for the Rp isomer. The effects of solvent and temperature on these vicinal couplings are described and the results are interpreted in terms of conformational shift towards the preferred ϵ t conformation. Chirality 14:814–818, 2002. © 2002 Wiley‐Liss, Inc.