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Determination of the anomeric configuration of 2′‐deoxy‐D‐ribonucleosides by 1 H NMR and by crystallographic studies of a novel 2′‐deoxy C ‐nucleoside
Author(s) -
Srivastava Prem C.,
Robbins Roland K.,
Takusagawa F.,
Berman H. M.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180838
Subject(s) - deoxyribonucleosides , chemistry , anomer , ribonucleoside , deoxyribonucleoside , nucleoside , stereochemistry , nuclear magnetic resonance spectroscopy , crystallography , methylene , organic chemistry , rna , enzyme , gene , biochemistry
2′‐Deoxy‐D‐ribonucleoside analogs of biologically active 2‐β‐D‐ribofuranosylthiazole‐4‐carboxamide were synthesized and the structure of the β anomer was determined by X‐ray crystallography and ′ 1 H nmr. 2′‐Methylene protons of α‐ and β‐deoxyribonucleosides were observed to exhibit characteristic patterns in the 1 H nmr which was used to distinguish between the two anomers. The method could be used to determine the anomeric configuration of both N‐ and C ‐2′‐deoxyribonucleosides.