title: Laspartomycin, an acidic lipopeptide antibiotic with a unique peptide core.
abstract: Laspartomycin was originally isolated and characterized in 1968 as a lipopeptide antibiotic related to amphomycin. The molecular weight and structure remained unknown until now. In the present study, laspartomycin was purified by a novel calcium chelate procedure, and the structure of the major component (1) was determined. The structure of laspartomycin C (1) differs from that of amphomycin and all related antibiotics as a result of its peptide region being acidic rather than amphoteric and the amino acid branching into the side chain being diaminopropionic rather than diaminobutyric. In addition, the fatty acid side chain is 2,3-unsaturated compared to 3,4-unsaturated for amphomycin and other related antibiotics. Calcium ion addition to stabilize a particular conformer was found to be important for an enzymatic deacylation of the antibiotic. A peptide resulting from the deacylation was critical for chemical structure determination by NMR studies, which also involved addition of calcium ions to stabilize a conformer.
authors.affiliation: BioSource Pharm, Inc., Spring Valley, NY 10977, USA. Biosource@prodigy.net
authors.forename: Donald B
authors.initials: DB
authors.lastname: Borders
authors.forename: Richard A
authors.initials: RA
authors.lastname: Leese
authors.forename: Howard
authors.initials: H
authors.lastname: Jarolmen
authors.forename: Noreen D
authors.initials: ND
authors.lastname: Francis
authors.forename: Amadeo A
authors.initials: AA
authors.lastname: Fantini
authors.forename: Tim
authors.initials: T
authors.lastname: Falla
authors.forename: John C
authors.initials: JC
authors.lastname: Fiddes
authors.forename: André
authors.initials: A
authors.lastname: Aumelas
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D055666:Lipopeptides; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D055666:Lipopeptides; D009842:Oligopeptides; D010456:Peptides, Cyclic; C519250:laspartomycin C; C004423:amphomycin