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

Abstract

Strategy for the solid-phase synthesis of nisin lipopeptide analogues using orthogonally protected lanthionines synthesised by ring-opening chemistry, and on-resin formation of dehydroalanine and dehydrobutyrine residues.

Synthesis of Fluorescent Lanthipeptide Cytolysin S Analogues by Late-Stage Sulfamidate Ring Opening

“…Cyclic sulfamidates have been extensively used for the regio- and stereoselective synthesis of a wide variety of chemicals through regioselective nucleophilic ring-opening reactions. − In particular, the intermolecular S-alkylation of five-membered ring sulfamidates has been exploited for the synthesis of orthogonally protected Lan and MeLan analogues. − For instance, the thioether ring B of haloduracin β as well as mimetics has been synthesized by intermolecular ring opening of sulfamidates with short cysteine-containing peptides. , However, attempts to achieve the intramolecular ring opening of peptides containing N -carbonyl sulfamidates and cysteine residues produced an unexpected N → S acyl shift …”