A conformationally constrained fused tricyclic nisin AB-ring system mimic toward an improved pyrophosphate binder of lipid II

Harmsen, R. A.G., Ghalit, N., Kemmink, J., Breukink, E., Liskamp, R. M.J. and Rijkers, D. T.S. (2014) A conformationally constrained fused tricyclic nisin AB-ring system mimic toward an improved pyrophosphate binder of lipid II. Tetrahedron, 70(42), pp. 7691-7699. (doi:10.1016/j.tet.2014.06.023)

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Abstract

The bacteria-specific membrane component lipid II is essential for bacterial cell wall synthesis. A tricyclic nisin mimic was designed and synthesized in which both thioether moieties were mimicked by an alkane-bridge, as well as the introduction of a third conformational constraint consisting of a macrocyclic lactam-bridge between the N-terminus and the B-ring. The newly designed tricyclic AB-ring mimic was found to bind lipid II since it was able to inhibit nisin-induced membrane leakage in a dose-dependent manner. These results imply that the tricyclic AB-ring mimic may form a novel class of lead structures for the development of nisin-based peptide antibiotics.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: Harmsen, R. A.G., Ghalit, N., Kemmink, J., Breukink, E., Liskamp, R. M.J., and Rijkers, D. T.S.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron
Publisher:Elsevier Ltd.
ISSN:0040-4020
ISSN (Online):1873-3581

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