Collect. Czech. Chem. Commun. 1987, 52, 2309-2316

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

Václav Čeřovskýa, Taťána Saksb and Karel Jošta

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
b Institute of Experimental Cardiology, Medical Academy of Sciences of U.S.S.R., 121552 Moscow, U.S.S.R.


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.