Versatile Selective α-Carboxylic
Acid Esterification of N-Protected Amino Acids and Peptides by Alcalase

Timo Nuijens; Claudia Cusan; John A. W. Kruijtzer; Dirk T. S. Rijkers; Rob M. J. Liskamp; Peter J. L. M. Quaedflieg

doi:10.1055/s-0028-1083362

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Synthesis 2009(5): 809-814
DOI: 10.1055/s-0028-1083362

PAPER

Versatile Selective α-Carboxylic Acid Esterification of N-Protected Amino Acids and Peptides by Alcalase

Timo Nuijens^a,b, Claudia Cusan^a, John A. W. Kruijtzer^b, Dirk T. S. Rijkers^b, Rob M. J. Liskamp^b, Peter J. L. M. Quaedflieg*^a
^a DSM Pharmaceutical Products, Innovative Synthesis & Catalysis, P.O. Box 18, 6160 Geleen, MD, The Netherlands
Fax: +31(46)4767604 ; e-Mail: peter.quaedflieg@dsm.com;
^b Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 Utrecht, TB, The Netherlands

Further Information

Publication History

Received 3 October 2008
Publication Date:
11 February 2009 (online)

Abstract
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Abstract

Under continuous removal of water, the industrial protease Alcalase allows selective synthesis of α-carboxylic acid methyl, ethyl, benzyl, allyl, 2-(trimethylsilyl)ethyl, and tert-butyl esters of amino acids and peptides under mild conditions in very high yields. The purified yields range from 72% to 92%.

Key words

enzymes - amino acids - esterification - esters - protecting groups

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