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Issue 31, 2012
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Thioester-isocyanides: versatile reagents for the synthesis of cycle–tail peptides

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Abstract

A novel class of reagents, thioester isocyanides, have been prepared and applied in the synthesis of peptide macrocycles. The isocyanide part of the molecule is deployed in a multicomponent macrocyclization step. This step is followed by chemoselective peptide ligation at the thioester part of the macrocycle. Our method can now be used for rapid assembly and evaluation of cycle–tail peptides.

Graphical abstract: Thioester-isocyanides: versatile reagents for the synthesis of cycle–tail peptides

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Supplementary files

Article information


Submitted
28 Sep 2011
Accepted
20 Feb 2012
First published
09 Mar 2012

Chem. Commun., 2012,48, 3775-3777
Article type
Communication

Thioester-isocyanides: versatile reagents for the synthesis of cycle–tail peptides

B. H. Rotstein, D. J. Winternheimer, L. M. Yin, C. M. Deber and A. K. Yudin, Chem. Commun., 2012, 48, 3775 DOI: 10.1039/C2CC16027G

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