Date of Award


Document Type

Thesis and Dissertation

Degree Name

Master of Science (MS)


Department of Chemistry

First Advisor

Richard W. Nagorski


It has been shown that carbinolamides are intermediates in the enzyme-catalyzed synthesis of -amidated peptides. Although carbinolamides are important intermediates in the production of these hormones and have roles in other biological venues, little attention has been given to their mechanisms of reaction in water, and, thus, it is difficult to speculate how their reaction would be enzymatically catalyzed. The purpose of the work presented here was to synthesize structural analogs of the biological intermediates and study their mechanism of breakdown in water. -Hydroxyhippuric acid, a substrate for the enzymatic system, provides an easily modified template for the study of the breakdown of this carbinolamide system. The pH-rate profiles for various aromatic substituted derivatives of -hydroxyhippuric acid will be presented, and the mechanism of the acid, hydroxide and buffer catalyzed reactions discussed.


Imported from Rafie_ilstu_0092N_11809.pdf


Page Count


Included in

Chemistry Commons