Tetrahedron: Asymmetry

α-Chymotrypsin-catalyzed peptide synthesis in frozen aqueous solution using N-protected amino acid carbamoylmethyl esters as acyl donors

SMA Salam, K Kagawa, K Kawashiro

Index: Salam, Sayed Mohiuddin Abdus; Kagawa, Ken-Ichi; Kawashiro, Katsuhiro Tetrahedron Asymmetry, 2006 , vol. 17, # 1 p. 22 - 29

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Citation Number: 19

Abstract

A kinetically controlled peptide synthesis catalyzed by α-chymotrypsin was performed in frozen aqueous solution (ice,− 24° C). The yield of the peptide was significantly improved by the use of the carbamoylmethyl (Cam) ester as the acyl donor instead of the conventional ethyl ester. The peptide yield increased up to ca. 90% when N-benzyloxycarbonyl (CBZ)- Phe-OCam and H-Phe-NH2 were used as the acyl donor and nucleophile, respectively. ...