Issue 30, 2012
From the journal:

Organic & Biomolecular Chemistry

Selective thioether macrocyclization of peptides having the N-terminal 2-chloroacetyl group and competing two or three cysteine residues in translation†‡

Kazuhiro Iwasaki,a   Yuki Goto,b   Takayuki Katohb  and  Hiroaki Suga*b  

* Corresponding authors

a Department of Chemistry and Biotechnology, Graduate School of Engineering, the University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan

b Department of Chemistry, Graduate School of Science, the University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8654, Japan
E-mail: hsuga@chem.s.u-tokyo.ac.jp

Abstract

The mode of thioether macrocyclization of peptides containing an N-terminal 2-chloroacetyl group and two or three competing cysteine residues at downstream positions has been extensively studied, leading to a strategy for designated formation of overlapping-bicyclic peptides or dumbbell-type bicyclic peptides.

Graphical abstract: Selective thioether macrocyclization of peptides having the N-terminal 2-chloroacetyl group and competing two or three cysteine residues in translation

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Article information

DOI
https://doi.org/10.1039/C2OB25306B
Article type
Communication
Submitted
11 Feb 2012
Accepted
29 Feb 2012
First published
01 Mar 2012

Org. Biomol. Chem., 2012,10, 5783-5786

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Selective thioether macrocyclization of peptides having the N-terminal 2-chloroacetyl group and competing two or three cysteine residues in translation

K. Iwasaki, Y. Goto, T. Katoh and H. Suga, Org. Biomol. Chem., 2012, 10, 5783 DOI: 10.1039/C2OB25306B

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