Issue 4, 2013
From the journal:

Chemical Communications

Simplifying alternating peptide synthesis by protease-catalyzed dipeptide oligomerization†

Xu Qin,a   Anne C. Khuong,a   Zheng Yu,a   Wenzhe Du,a   John Decaturb  and  Richard A. Gross*a  

* Corresponding authors

a 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, USA
E-mail: rgross@poly.edu
Tel: +1 718-260-3024

b Department of Chemistry, Columbia University, 3000 Broadway, New York, New York, USA
E-mail: jdd13@columbia.edu

Abstract

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.

Graphical abstract: Simplifying alternating peptide synthesis by protease-catalyzed dipeptide oligomerization

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Article information

DOI
https://doi.org/10.1039/C2CC36381J
Article type
Communication
Submitted
01 Sep 2012
Accepted
19 Nov 2012
First published
20 Nov 2012

Chem. Commun., 2013,49, 385-387

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Simplifying alternating peptide synthesis by protease-catalyzed dipeptide oligomerization

X. Qin, A. C. Khuong, Z. Yu, W. Du, J. Decatur and R. A. Gross, Chem. Commun., 2013, 49, 385 DOI: 10.1039/C2CC36381J

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