Structural and conformational analysis of two native procyanidin trimers.
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.
Tarascou
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Laboratoire de Chimie Organique et Organométallique, UMR 5802-CESAMO, Université de Bordeaux 1, 351 cours de la Libération, 33405 Talence, France.
Ducasse
Marie-Agnès
MA
Dufourc
Erick J
EJ
Moskau
Detlef
D
Fouquet
Eric
E
Laguerre
Michel
M
Pianet
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D044946:Biflavonoids / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002392:Catechin / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011108:Polymers / Q000737:chemistry; D044945:Proanthocyanidins / Q000737:chemistry*
D044946:Biflavonoids; D011108:Polymers; D044945:Proanthocyanidins; C017674:procyanidin; D002392:Catechin