title: Structure and biosynthesis of carnolysin, a homologue of enterococcal cytolysin with D-amino acids.
abstract: Lantibiotics are a group of highly post-translationally modified bacterial antimicrobial peptides characterized by the presence of the thioether-containing amino acids lanthionine and methyllanthionine. Carnobacterium maltaromaticum C2 was found to produce a two-component lantibiotic homologous to enterococcal cytolysin. Through tandem mass spectrometry and NMR spectroscopy, the post-translational modifications of carnolysin were established, and the topologies of the lanthionine and methyllanthionine rings were determined. Chiral GC-MS analysis revealed that, like cytolysin, carnolysin contained lanthionine and methyllanthionine residues of unusual stereochemistry. Carnolysin, unlike cytolysin, was shown to contain d-alanine and unprecedented D-aminobutyrate derived from serine and threonine, respectively. Carnolysin was heterologously expressed in Escherichia coli, demonstrating that reductase CrnJ is involved in the formation of the D-amino acids.
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta, Canada , T6G 2G2.
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Lohans
authors.forename: Jessica L
authors.initials: JL
authors.lastname: Li
authors.forename: John C
authors.initials: JC
authors.lastname: Vederas
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry*; D023181:Antimicrobial Cationic Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D001430:Bacteriocins / Q000138:chemical synthesis / Q000737:chemistry*; D056568:Carnobacteriaceae / Q000737:chemistry*; D016983:Enterococcus / Q000737:chemistry; D008745:Methylation; D008969:Molecular Sequence Data; D054353:Perforin / Q000138:chemical synthesis / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D000900:Anti-Bacterial Agents; D023181:Antimicrobial Cationic Peptides; D001430:Bacteriocins; D013440:Sulfides; C000602010:carnolysin; D054353:Perforin; C001520:lanthionine; D000409:Alanine