title: Biochemical, structural, and genetic characterization of tridecaptin A₁, an antagonist of Campylobacter jejuni.
abstract: Bacillus circulans NRRL B-30644 (now Paenibacillus terrae) was previously reported to produce SRCAM 1580, a bacteriocin active against the food pathogen Campylobacter jejuni. We have been unable to isolate SRCAM 1580, and did not find any genetic determinants in the genome of this strain. We now report the reassignment of this activity to the lipopeptide tridecaptin A₁. Structural characterization of tridecaptin A1 was achieved through NMR, MS/MS and GC-MS studies. The structure was confirmed through the first chemical synthesis of tridecaptin A₁, which also revealed the stereochemistry of the lipid chain. The impact of this stereochemistry on antimicrobial activity was examined. The biosynthetic machinery responsible for tridecaptin production was identified through bioinformatic analyses. P. terrae NRRL B-30644 also produces paenicidin B, a novel lantibiotic active against Gram-positive bacteria. MS/MS analyses indicate that this lantibiotic is structurally similar to paenicidin A.
authors.affiliation: Department of Chemistry, University of Alberta, 11227 Saskatchewan Drive, Edmonton, Alberta T6G 2G2 (Canada).
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Lohans
authors.forename: Marco J
authors.initials: MJ
authors.lastname: van Belkum
authors.forename: Stephen A
authors.initials: SA
authors.lastname: Cochrane
authors.forename: Zedu
authors.initials: Z
authors.lastname: Huang
authors.forename: Clarissa S
authors.initials: CS
authors.lastname: Sit
authors.forename: Lynn M
authors.initials: LM
authors.lastname: McMullen
authors.forename: John C
authors.initials: JC
authors.lastname: Vederas
mesh_terms: D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D001430:Bacteriocins / Q000096:biosynthesis / Q000737:chemistry; D016123:Campylobacter jejuni / Q000187:drug effects*; D008055:Lipids / Q000737:chemistry; D055666:Lipopeptides / Q000096:biosynthesis / Q000737:chemistry* / Q000494:pharmacology*; D008969:Molecular Sequence Data; D005810:Multigene Family; D056507:Paenibacillus / Q000235:genetics / Q000378:metabolism; D010455:Peptides / Q000737:chemistry* / Q000235:genetics / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D001430:Bacteriocins; D008055:Lipids; D055666:Lipopeptides; D010455:Peptides; C017770:tridecaptins
keywords: antimicrobial agents; bacteriocins; lipopeptides; peptides; structure elucidation