pH-Rate profile and buffer catalysis of the reaction of a novel series of N-(hydroxybenzyl)acetamides

ORGN 444

Matthew F. Sansone, mfsanso@ilstu.edu and Richard W. Nagorski, rnagor@ilstu.edu. Department of Chemistry, Illinois State University, Box 4160, Normal, IL 61790-4160
Carbonolamides are a fundamentally important functionality in many biological processes. For example, carbonolamides are intermediates in the biosynthesis of mammalian alpha-amidated peptides. Despite the importance of carbinolamides in these processes, very little work has been done to understand the affect of structure on the reactivity of these compounds. The lack of prior studies involving structural variation of the aldehyde portion of the carbinolamide can be traced back to synthetic limitations. In the work presented here, these limitations have been overcome, a new class of carbinolamides has been synthesized, and the kinetic studies as a function of pH, as well as preliminary study of buffer catalysis are reported.