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.
Recommended Citation
Wang, Yonggang, "Reaction of Caffeic Acid with Amino Acids" (2000). Masters Theses. 4342.
https://scholarworks.wmich.edu/masters_theses/4342