Open Access

ARTICLE

Papain Catalyzed Synthesis of Protected Amino Acid Amides

Leendert W. Schwab, Wouter M. J. Kloosterman, Jakob Konieczny, Katja Loos^*

Department of Polymer Chemistry & Zernike Institute for Ad vanced Materials, University of Groningen, Nijenborgh 4, 9747AG Groningen, The Netherlands

* Corresponding Author:

Journal of Renewable Materials 2013, 1(1), 73-78. https://doi.org/10.7569/JRM.2012.634102

Received 13 July 2012; Accepted 19 October 2012;

Abstract

The papain catalyzed enzymatic synthesis of amido amines catalyzed from aromatic diamines and N-carbobenzyloxy (Z) protected amino acids (Gly, L-Leu, L-Phe) is described. The amides precipitate (yield 19–47 % depending on the amino acid used) from the reaction mixture after one amide bond is formed thus preventing the formation of diamides in all cases. Papain retains its activity in buffers with a higher pH (9 and 12) observable by the amide bond formation between 1,3-phenylene diamine and Z-L-Gly and Z-L-Phe. Aliphatic diamines (1,4-butanediamine and 1,6-hexanediamine) were used as well but amide formation could not be observed in buffers of pH 7, 9 or 12 due to the selectivity of papain.

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Keywords

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