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

Kazuhiro Iwasaki; Yuki Goto; Takayuki Katoh; Hiroaki Suga

doi:10.1039/C2OB25306B

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Organic & Biomolecular Chemistry

Issue 30, 2012

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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

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

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

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

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

DOI: 10.1039/C2OB25306B
Received 11 Feb 2012, Accepted 29 Feb 2012
First published online 01 Mar 2012

This article is part of themed collection: Organic & Biomolecular Chemistry 10th Anniversary

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Abstract
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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.