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Conformational Analysis of Oligomeric Proanthocyanidins

  • Chapter
Chemistry and Significance of Condensed Tannins

Abstract

The conformational behavior of polymers of 2,3-trans- and 2,3-cis-flavan3-ols [(+)-catechin and (−)-epicatechin] depends on the population of dihedral angles at the interflavan bond and the conformation of the heterocyclic rings. The behavior of the heterocyclic rings can be determined by study of the monomers and dimers. The results obtained from x-ray diffraction and MM2 calculations are reviewed here. Conformations at the interflavan bond are studied by MM2 calculations, high resolution 1H-NMR, and time-resolved fluorescence. The implications of these results are that 4β → 8 linked polymers are random coils with dimensions somewhat smaller than those of unperturbed polystyrene chains of the same molecular weight. The dimensions of polymers with 4β → 6 links are not much different.

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Authors and Affiliations

  1. Institute of Polymer Science, The University of Akron, Akron, Ohio, 44325, USA

    Wayne L. Mattice

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  1. Wayne L. Mattice
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Editors and Affiliations

  1. United States Department of Agriculture, Pineville, Louisiana, USA

    Richard W. Hemingway

  2. Oregon State University, Corvallis, Oregon, USA

    Joseph J. Karchesy

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© 1989 Plenum Press, New York

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Mattice, W.L. (1989). Conformational Analysis of Oligomeric Proanthocyanidins. In: Hemingway, R.W., Karchesy, J.J., Branham, S.J. (eds) Chemistry and Significance of Condensed Tannins. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-7511-1_7

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  • DOI: https://doi.org/10.1007/978-1-4684-7511-1_7

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-7513-5

  • Online ISBN: 978-1-4684-7511-1

  • eBook Packages: Springer Book Archive

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