Issue 0, 1980

Polymeric proanthocyanidins. Stereochemistry, structural units, and molecular weight

Abstract

Homogeneous polymeric proanthocyanidins have been isolated from 22 plant sources and all are based on a C(4)–C(8)[or C(6)] linked polyflavan-3-ol structure. 13C N.m.r, spectroscopy in 2[H6]acetone–water is used to calculate the ratio of procyanidin to prodelphinidin monomer units, the average heterocyclic ring stereochemistry of the monomers, and the ratio of monomers to chain-terminating units. The majority of polymers isolated in this study possess monomers with predominantly a 2,3-cis stereochemistry [the same configuration as (–)-epicatechin]. The number-average molecular weight, calculated from monomer to terminal unit ratios, of the polymers is 1 500–5 000. The structure of the chain-terminating group is established by thiolysis degradation and g.l.c. analysis of the products.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1980, 2278-2286

Polymeric proanthocyanidins. Stereochemistry, structural units, and molecular weight

Z. Czochanska, L. Y. Foo, R. H. Newman and L. J. Porter, J. Chem. Soc., Perkin Trans. 1, 1980, 2278 DOI: 10.1039/P19800002278

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