Versatile and stereoselective syntheses of orthogonally protected beta-methylcysteine and beta-methyllanthionine.
[reaction: see text] Lantibiotics are a class of lanthionine (and/or beta-methyllanthionine)-containing peptides with antibioitic activity against Gram-positive bacteria. As part of our research effort directed toward the synthesis and mechanistic study of the lantibiotic peptide mersacidin (1), we report stereoselective syntheses of orthogonally protected beta-methylcysteine (beta-MeCys) and beta-methyllanthionine (beta-MeLan), two key nonnatural amino acid components of the mersacidin architecture.
Narayan
Radha S
RS
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, MC 0358, La Jolla, California 92093, USA.
Vannieuwenhze
Michael S
MS
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000595:Amino Acid Sequence; D001388:Aziridines / Q000737:chemistry; D002384:Catalysis; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry*; D013912:Threonine / Q000737:chemistry
D001388:Aziridines; D013440:Sulfides; D013912:Threonine; C005080:beta-methyllanthionine; C008425:S-methylcysteine; D003545:Cysteine; D000409:Alanine