SOLUTION CONFORMATIONS AND HYDROLYTIC STABILITY OF 2 '-SUBSTITUTED AND 3'-SUBSTITUTED 2',3'-DIDEOXYRIBONUCLEOSIDES, INCLUDING SOME POTENTIAL INHIBITORS OF HUMAN-IMMUNODEFICIENCY-VIRUS



: OKSMAN P, HAKALA H, ZAVGORODNY S, POLIANSKI M, AZHAYEV A, VANAERSCHOT A, HERDEWIJN P, LONNBERG H

Publisher: JOHN WILEY & SONS LTD

: 1992

Journal of Physical Organic Chemistry

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY

: J PHYS ORG CHEM

: 5

: 11

: 741

: 747

: 7

: 0894-3230

DOI: https://doi.org/10.1002/poc.610051106


Sugar ring conformations of a number of 2'- and 3'-substituted 2',3'-dieoxyribonudeosides were determined in (H2O)-H-2 by H-1 NMR spectroscopy. First-order rate constants for the cleavage of their N-glycosidic bond in aqueous acid were measured. The dependence of sugar ring conformation and hydrolytic stability on the polar nature of the 2'/3'-substitutent is discussed.



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