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

Slootweg, J. C., Kemmink, J., Liskamp, R. M. J. and Rijkers, D. T. S. (2013) Synthesis and structural characterization of the individual diastereoisomers of a cross-stapled alkene-bridged nisin DE-ring mimic. Organic and Biomolecular Chemistry, 11(43), pp. 7486-7496. (doi:10.1039/c3ob41359d)

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Publisher's URL: http://dx.doi.org/10.1039/c3ob41359d

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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: Slootweg, J. C., Kemmink, J., Liskamp, R. M. J., and Rijkers, D. T. S.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
Publisher:Royal Society of Chemistry
ISSN:1477-0520
ISSN (Online):1477-0539

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