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Issue 20, 2011
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Microwave-assisted chemical ligation of S-acyl peptides containing non-terminal cysteine residues

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Abstract

An efficient approach for the synthesis of a series of S-acyl peptides containing internal cysteine residues has been developed and the chemical long-range ligation of these S-acyl peptidesvia 5-, 8-, 11- and 14-membered cyclic transition states has been investigated. Our results include the first examples of successful isopeptide ligations starting from S-acyl peptides containing non-terminal cysteine residues and indicate that the cyclic transition states studied in this present paper are decreasingly favored in the order of their sizes 5≫14>11≫8.

Graphical abstract: Microwave-assisted chemical ligation of S-acyl peptides containing non-terminal cysteine residues

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Publication details

The article was received on 11 May 2011, accepted on 29 Jun 2011 and first published on 29 Jun 2011


Article type: Paper
DOI: 10.1039/C1OB05740E
Citation: Org. Biomol. Chem., 2011,9, 7162-7167
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    Microwave-assisted chemical ligation of S-acyl peptides containing non-terminal cysteine residues

    F. K. Hansen, K. Ha, E. Todadze, A. Lillicotch, A. Frey and A. R. Katritzky, Org. Biomol. Chem., 2011, 9, 7162
    DOI: 10.1039/C1OB05740E

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