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Structural and conformational analysis of two native procyanidin trimers
Author(s) -
Tarascou Isabelle,
Ducasse MarieAgnès,
Dufourc Erick J.,
Moskau Detlef,
Fouquet Eric,
Laguerre Michel,
Pianet Isabelle
Publication year - 2007
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.1938
Subject(s) - chemistry , conformational isomerism , stacking , crystallography , stereochemistry , proanthocyanidin , trimer , carbon atom , molecular mechanics , molecular dynamics , computational chemistry , molecule , organic chemistry , dimer , polyphenol , antioxidant , alkyl
The structure and conformation of two native procyanidin trimers in water have been determined using 2D NMR and molecular mechanics. The results show the existence of four rotameric forms, one of which is predominant (60 to 80%). These four rotamers are shown to be in slow to intermediate exchange on the NMR timescale. Both trimers, whose structures vary owing to a different substitution of one carbon atom, adopt conformations in which stacking between different phenolic rings is favored. Copyright © 2006 John Wiley & Sons, Ltd.