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Conformational study of fosinopril sodium in solution using NMR and molecular modeling
Author(s) -
Liu Songbai,
Shi Yanhong,
Zhang Qingwen,
Song Guoqiang
Publication year - 2003
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1230
Subject(s) - chemistry , conformational isomerism , stacking , amide , stereochemistry , methanol , crystallography , molecule , computational chemistry , organic chemistry
Abstract Two conformers of fosinopril sodium in methanol were unambiguously established using 2D NMR methods and variable‐temperature NMR experiments. Differences in their conformational structure were shown to be related to the rotational energy barrier about the amide bond and hydrophobic interaction. The relationship between the 3D structure and activity is discussed. It is suggested that the trans ‐conformer may be more biologically active owing to its stacking structure and strong hydrophobic interaction and the cis ‐conformer could be more easily hydrolyzed because of its extended structure. Copyright © 2003 John Wiley & Sons, Ltd.