Author

Wang

Date of Award

8-2000

Degree Name

Master of Arts

Department

Chemistry

First Advisor

Dr. Donald R. Schreiber

Second Advisor

Dr. James Howell

Third Advisor

Dr. Michael McCarville

Fourth Advisor

Dr. Subra Muralidharan

Access Setting

Masters Thesis-Open Access

Abstract

The reaction of caffeic acid with tryptophan was studied as a model for the reaction of caffeic acid with amino acids in the aquatic environment. Although the autoxidation reaction of caffeic acid in aqueous solution with subsequent dimerization had been previously studied, it was examined as well for comparison purposes. The present studies demonstrate that oxidized caffeic acid would react with tryptophan. The reaction, like the dimerization reaction, was catalyzed by the presence of iron(III) ions at low pH ( <4) and by hydroxide ions at high pH (10). The reaction of caffeic acid with itself yielded six products, four of which were identified by mass spectroscopy as dimers, with the other two being trimers. The reaction of caffeic acid with tryptophan yielded three product peaks. Two of the product peaks had similar retention times to the dimers from the self-reaction of caffeic acid; the third was a new product resulting from the reaction of caffeic acid with the tryptophan.

A mechanism for the reaction of caffeic acid with tryptophan has been proposed. This mechanism was based on the analysis of the products and previous mechanisms presented by earlier workers for the caffeic acid self-reaction.

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Chemistry Commons

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