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Angew Chem Int Ed Engl. 2013 Oct 25;52(44):11530-3. doi: 10.1002/anie.201305839. Epub 2013 Sep 13.

Remarkable biomimetic chemoselective aerobic oxidation of flavano-ellagitannins found in oak-aged wine.

Author information

1
Université de Bordeaux, Institut des Sciences Moléculaires (CNRS-UMR 5255) and Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex (France).

Abstract

Under the auspices of Bacchus! Acutissimins, natural flavano-ellagitannins, occur in oak-aged wine as a result of a diastereoselective condensation reaction of the flavan-3-ol catechin, a component of grapes, with the C-glucosidic ellagitannin vescalagin, found in oak. The acutissimins are further converted into natural mongolicains and analogues of camelliatannin G in a remarkably chemoselective fashion by simple aerobic oxidation.

KEYWORDS:

biosynthesis; chemoselectivity; oxidation; tannins; wine

PMID:
24039115
DOI:
10.1002/anie.201305839
[Indexed for MEDLINE]

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