Ring-opening reactions for the solid-phase synthesis of nisin lipopeptide analogues?

Organic & Biomolecular Chemistry Pub Date: 2022-11-03 DOI: 10.1039/D2OB01526A

Abstract

Three lipopeptide analogues of the lantibiotic nisin A have been synthesised on-resin using Fmoc-SPPS techniques to investigate the structure–activity relationship of the A and B ring of these types of lanthipeptides. Lanthionine and methyllanthionine macrocycles were incorporated using orthogonally protected residues for on-resin cyclisation. Unsaturated dehydroalanine and, for the first time, dehydrobutyrine were synthesised on-resin from their cysteine derivatives. However, none of the synthetic or semi-synthetic lipopeptide analogues of nisin showed inhibitory activity towards bacterial strains that are normally sensitive to nisin.

Graphical abstract: Ring-opening reactions for the solid-phase synthesis of nisin lipopeptide analogues
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