Papain-catalyzed synthesis of 2-naphthylamides of N-acylamino acids and dipeptides

Abstract

2-Naphthylamides of several N-acylamino acids were prepared by papain-catalyzed condensation reaction in acidic medium. Under the same conditions, papain catalyzed the synthesis of peptide bond between benzyloxycarbonylglycine and phenylalanine 2-naphthylamide and between benzyloxycarbonylserine and tyrosine 2-naphthylamide. Phenylalanine 2-naphthylamide was also acylated with benzyloxycarbonyl glycine methyl ester in an alkaline medium. For comparison, papain-catalyzed condensations of benzyloxycarbonyl-S-benzylcysteine or benzyloxycarbonylalanine with aniline and its derivatives, benzylamine, phenylhydrazine, cyclohexylamine and 1-naphthylamine, were studied.