Determination of the anomeric configuration of 2′‐deoxy‐D‐ribonucleosides by 1H NMR and by crystallographic studies of a novel 2′‐deoxy C‐nucleoside

Prem C. Srivastava, Roland K. Robbins, F. Takusagawa, H. M. Berman

Research output: Contribution to journalLetterpeer-review

50 Scopus citations

Abstract

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 ′1H nmr. 2′‐Methylene protons of α‐ and β‐deoxyribonucleosides were observed to exhibit characteristic patterns in the 1H 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.

Original languageEnglish (US)
Pages (from-to)1659-1662
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume18
Issue number8
DOIs
StatePublished - Dec 1981
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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