Penicillin acylase-catalyzed peptide synthesis in aqueous medium: a chemo-enzymatic route to stereoisomerically pure diketopiperazines

…, AV Korennykh, LM van Langen, F van Rantwijk…

Index: Khimiuk, Andrei Y.; Korennykh, Alexei V.; Van Langen, Luuk M.; Van Rantwijk, Fred; Sheldon, Roger A.; Svedas, Vytas K. Tetrahedron Asymmetry, 2003 , vol. 14, # 20 p. 3123 - 3128

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Citation Number: 22

Abstract

A range of non-natural dipeptides of the general formula d-(−)-phenylglycyl-lX, where X is a natural α-amino acid, have been prepared by penicillin acylase-catalyzed synthesis in aqueous medium from d-(−)-phenylglycine amide and the corresponding amino acids. The conversion of the dipeptides to the corresponding dipeptide esters, followed by their subsequent spontaneous cyclization afforded the corresponding stereoisomerically pure ...