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- W2072474312 endingPage "1554" @default.
- W2072474312 startingPage "1540" @default.
- W2072474312 abstract "This report describes the design, synthesis, and biochemical evaluation of alkene- and alkane-bridged AB(C)-ring mimics of the lantibiotic nisin. Nisin belongs to a class of natural antimicrobial peptides, and has a unique mode of action: its AB(C)-ring system binds to the pyrophosphate moiety of lipid II. This mode of action was the rationale for the design of smaller nisin-derived peptides to obtain novel potential antibiotics. As a conformational constraint the thioether bridge was mimicked by an alkene- or alkane isostere. The peptides of the linear individual ring precursors were synthesized on solid support or in solution, and cyclized by ring-closing metathesis in solution with overall yields of between 36 and 89 %. The individual alkene-bridged macrocycles were assembled in solution by using carbodiimide-based synthesis protocols for the corresponding AB(C)-ring mimics. These compounds were tested for their binding affinity toward lipid II by evaluation of their potency to inhibit nisin-induced carboxyfluorescein release from large unilamellar vesicles. It was found that these AB(C)-ring mimics were not able to induce membrane leakage; however, they acted by inhibiting nisin-induced carboxyfluorescein release; this indicates their affinity toward lipid II. These results imply that an alkene or alkane moiety is a suitable thioether bridge mimic." @default.
- W2072474312 created "2016-06-24" @default.
- W2072474312 creator A5013944488 @default.
- W2072474312 creator A5020444863 @default.
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- W2072474312 creator A5054936232 @default.
- W2072474312 creator A5060532074 @default.
- W2072474312 creator A5063361074 @default.
- W2072474312 date "2007-08-27" @default.
- W2072474312 modified "2023-10-17" @default.
- W2072474312 title "Synthesis of Bicyclic Alkene-/Alkane-Bridged Nisin Mimics by Ring-Closing Metathesis and their Biochemical Evaluation as Lipid II Binders: toward the Design of Potential Novel Antibiotics" @default.
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- W2072474312 doi "https://doi.org/10.1002/cbic.200700244" @default.
- W2072474312 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/17674393" @default.