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Reactions at the A-ring of Proanthocyanidins

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Book cover Chemistry and Significance of Condensed Tannins

Abstract

The most common reactions at the A-ring of proanthocyanidins (condensed tannins) are examples of electrophilic aromatic substitution where an electrophile displaces a hydrogen (i.e., at C-6 and/or C-8 of procyanidins and profisetinidins). Other types of displacements include dehalogenation, procyanidin degradation, and oxidative free-radical coupling. The hydroxylation pattern of the A-ring controls both reactivity and orientation of substitution, partially by steric effects, but electronic factors have more influence. Examples of A-ring reactions include those of commercial interest (methylolation, condensation) and of diagnostic interest (halogenation, alkylation, hydrogen/deuterium exchange). C- and O-glycosylation are further types of A-ring reactions leading to natural products.

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  1. Department of Chemistry, Louisiana College, Pineville, Louisiana, 71360, USA

    G. Wayne McGraw

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  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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McGraw, G.W. (1989). Reactions at the A-ring of 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_14

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