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Issue 8, 2008
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Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides

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Abstract

The naturally-occurring cyclic cystine-knot microprotein trypsin inhibitors MCoTI-I and MCoTI-II have been synthesised using both thia-zip native chemical ligation and a biomimetic strategy featuring chemoenzymatic cyclisation by an immobilised protease. Engineered analogues have been produced containing a range of substitutions at the P1 position that redirect specificity towards alternative protease targets whilst retaining excellent to moderate affinity. Furthermore, we report an MCoTI analogue that is a selective low-µM inhibitor of foot-and-mouth-disease virus (FMDV) 3C protease, the first reported peptide-based inhibitor of this important viral enzyme.

Graphical abstract: Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides

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Publication details

The article was received on 30 Jan 2008, accepted on 15 Feb 2008 and first published on 06 Mar 2008


Article type: Paper
DOI: 10.1039/B801667D
Citation: Org. Biomol. Chem., 2008,6, 1462-1470
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    Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides

    P. Thongyoo, N. Roqué-Rosell, R. J. Leatherbarrow and E. W. Tate, Org. Biomol. Chem., 2008, 6, 1462
    DOI: 10.1039/B801667D

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