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Issue 43, 2013
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Synthesis and structural characterization of the individual diastereoisomers of a cross-stapled alkene-bridged nisin DE-ring mimic

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Abstract

Herein, we describe the synthesis, structural characterization, and synthetic use as an advanced intermediate of a cross-stapled alkene-bridged hexapeptide to mimic the DE-ring of the lantibiotic nisin. The linear precursor was cyclized by ring-closing metathesis to give the correctly folded bicyclic hexapeptide in a single step, and the four individual diastereoisomers were isolated, structurally assigned and characterized by HPLC, NMR and MS, respectively. The bicyclic hexapeptide was used as a versatile advanced synthon and was modified at its C- and N-terminus, among others, with an azide moiety to access a building block suitable for Cu(I)-catalyzed alkyne–azide cycloaddition-based ligation reactions.

Graphical abstract: Synthesis and structural characterization of the individual diastereoisomers of a cross-stapled alkene-bridged nisin DE-ring mimic

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Publication details

The article was received on 03 Jul 2013, accepted on 09 Sep 2013 and first published on 09 Sep 2013


Article type: Paper
DOI: 10.1039/C3OB41359D
Citation: Org. Biomol. Chem., 2013,11, 7486-7496
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    Synthesis and structural characterization of the individual diastereoisomers of a cross-stapled alkene-bridged nisin DE-ring mimic

    J. C. Slootweg, J. Kemmink, R. M. J. Liskamp and D. T. S. Rijkers, Org. Biomol. Chem., 2013, 11, 7486
    DOI: 10.1039/C3OB41359D

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