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Issue 76, 2013
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Synthesis of cyclic peptide hemicryptophanes: enantioselective recognition of a chiral zwitterionic guest

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Abstract

The synthesis of the first members of a new class of cyclic peptide-containing hemicryptophanes is described. Synthesis was achieved through attachment of veratryl groups to the L-tyrosine side chains of a cyclic hexapeptide, c(YG)3, followed by intramolecular cyclodehydration to generate the CTV unit. The diastereomeric P- and M-hemicryptophanes were generated in a 2 : 1 ratio and were separated by chromatography. The enantioselective binding properties of the hemicryptophanes were investigated by complexation with carnitine. Both isomers were found to have significant selectivity for binding (R)-carnitine.

Graphical abstract: Synthesis of cyclic peptide hemicryptophanes: enantioselective recognition of a chiral zwitterionic guest

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Publication details

The article was received on 26 Jun 2013, accepted on 01 Aug 2013 and first published on 01 Aug 2013


Article type: Communication
DOI: 10.1039/C3CC44784G
Citation: Chem. Commun., 2013,49, 8504-8506
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    Synthesis of cyclic peptide hemicryptophanes: enantioselective recognition of a chiral zwitterionic guest

    J. R. Cochrane, A. Schmitt, U. Wille and C. A. Hutton, Chem. Commun., 2013, 49, 8504
    DOI: 10.1039/C3CC44784G

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