Simplifying alternating peptide synthesis by protease-catalyzed dipeptide oligomerization.

Chem Commun (Camb)

Center for Biocatalysis and Bioprocessing of Macromolecules, Department of Chemical and Biomolecular Engineering, Polytechnic Institute of New York University, 6 Metrotech Center, Brooklyn, New York 11201, USA.

Published: January 2013

A unique route to perfectly alternating oligopeptides is described. First, AG-OEt was prepared by standard chemical coupling. Then, AG-OEt was converted by papain-catalysis in 30 s to (AG)(x) (80%-yield, x = 9.4 ± 0.3). Extension of this strategy to other alternating peptide compositions as well as the importance of selecting a protease and reaction conditions that avoid competing transamidation and hydrolysis reactions is discussed.

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Source
http://dx.doi.org/10.1039/c2cc36381jDOI Listing

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