A concise stereoselective synthesis of orthogonally protected lanthionine and beta-methyllanthionine.
Lantibiotics such as nisin are active against most Gram-positive bacteria and constitute an important class of antibacterial agents. These ribosomally synthesized peptides contain either one or both of the unusual amino acids meso-lanthionine (m-Lan) or beta-methyllanthionine (beta-MeLan). Nucleophilic ring opening of sulfamidates allows facile preparation of stereochemically pure derivatives of m-Lan and beta-MeLan with orthogonal protection for solid phase synthesis of lantibiotic analogues.
Cobb
Steven L
SL
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada. john.vederas@ualberta.ca.
Vederas
John C
JC
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D001430:Bacteriocins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*
D001430:Bacteriocins; D013440:Sulfides; C005080:beta-methyllanthionine; C001520:lanthionine; D000409:Alanine