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

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

Org Biomol Chem. 2012 Aug 14;10(30):5783-6. doi: 10.1039/c2ob25306b. Epub 2012 Mar 14.

Authors

Kazuhiro Iwasaki¹, Yuki Goto, Takayuki Katoh, Hiroaki Suga

Affiliation

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

PMID: 22419118
DOI: 10.1039/c2ob25306b

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acid Sequence
Cyclization
Cysteine / chemistry*
Molecular Sequence Data
Peptides / chemistry*
Peptides / metabolism*
Protein Biosynthesis*
Protein Engineering / methods*
Sulfides / chemistry*

Substances

Peptides
Sulfides
Cysteine