Concise preparation of tetra-orthogonally protected (2S,6R)-lanthionines.
Lantibiotics are antimicrobial peptides containing the unique bis-amino acids lanthionine and beta-methyllanthionine. While previous syntheses of lanthionine have often involved the coupling of precursors derived from D-serine and L-cysteine, we here report an inverted strategy whereby D-cysteine and L-serine are employed as building blocks. This approach provides for a concise preparation of tetra-orthogonally protected (2R,6S)-lanthionines while allowing convenient introduction of orthogonal protecting groups not previously incorporated into lanthionines.
Martin
Nathaniel I
NI
Department of Medicinal Chemistry and Chemical Biology, University of Utrecht, Sorbonnelaan 16, 3584 CA Utrecht, The Netherlands. n.i.martin@uu.nl
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001430:Bacteriocins / Q000737:chemistry; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
D001430:Bacteriocins; D013440:Sulfides; C001520:lanthionine; D000409:Alanine