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Issue 3, 2013
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A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines

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Abstract

A novel and traceless strategy has been devised that allows a coupling of thioacids and dithiocarbamate-terminal amines. This strategy had been assumed to be dependent on the attachment of a functional equivalent of a cysteine side chain in earlier native chemical ligation approaches. This approach enables the traceless removal of CS2 to directly generate the desired amide bond and is compatible with a range of unprotected side chains of amino acid. The ability to produce amide or peptides by a traceless removal of the auxiliary is a significant virtue of the method. Meanwhile, the application of this new peptide-bond-forming reaction to the synthesis of novel endomorphin (EM) derivatives with various binding potencies was realized.

Graphical abstract: A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines

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Publication details

The article was received on 21 Aug 2012, accepted on 21 Nov 2012 and first published on 22 Nov 2012


Article type: Edge Article
DOI: 10.1039/C2SC21317F
Citation: Chem. Sci., 2013,4, 970-976
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    A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines

    W. Chen, J. Shao, M. Hu, W. Yu, M. A. Giulianotti, R. A. Houghten and Y. Yu, Chem. Sci., 2013, 4, 970
    DOI: 10.1039/C2SC21317F

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