Glycolamide esters of N-acylamino acids and peptides

Abstract

The glycolamide esters, RNHCHR'CO2CH2CONH2, of several N-acylamino acids have been prepared. Model experiments indicate that the glycolamide group possesses weak acylating ability in simple peptide coupling reactions, but that it can be dehydrated under mild conditions with formation of cyanomethyl esters, which are known to be active acylating agents. The possible application of the glycolamide derivatives in peptide synthesis is considered. A number of protected dipeptide glycolamide esters were also synthesized.