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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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Publication details

The article was received on 28 Sep 2011, accepted on 20 Feb 2012 and first published on 09 Mar 2012


Article type: Communication
DOI: 10.1039/C2CC16027G
Citation: Chem. Commun., 2012,48, 3775-3777
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    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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