title: Structure and biosynthesis of scabichelin, a novel tris-hydroxamate siderophore produced by the plant pathogen Streptomyces scabies 87.22.
abstract: Scabichelin and turgichelin, novel tris-hydroxamate siderophores, were isolated from Streptomyces antibioticus NBRC 13838/Streptomyces scabies JCM 7914 and Streptomyces turgidiscabies JCM 10429, respectively. The planar structures of scabichelin and turgichelin were elucidated by mass spectrometry, and 1- and 2-D NMR spectroscopic analyses of their gallium(III) complexes. The relative and absolute stereochemistry of the metabolites was determined by the modified Marfey's method in conjunction with computational modelling and NOESY NMR analysis of Ga-scabichelin and Ga-turgichelin. Genome sequence analysis of the plant pathogen Streptomyces scabies 87.22 identified a gene cluster containing a gene encoding a nonribosomal peptide synthetase (NRPS) that was predicted to direct the production of a pentapeptide with structural similarities to scabichelin and turgichelin. Comparative LC-MS/MS analyses of iron-deficient culture supernatants from wild type S. scabies 87.22 and a mutant in which the NRPS gene had been disrupted, and scabichelin purified from S. antibioticus, showed that scabichelin is the metabolic product of the cryptic gene cluster, strongly suggesting that it functions as a siderophore.
authors.affiliation: Department of Agriculture, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan.
authors.forename: Shinya
authors.initials: S
authors.lastname: Kodani
authors.forename: Joanna
authors.initials: J
authors.lastname: Bicz
authors.forename: Lijiang
authors.initials: L
authors.lastname: Song
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Deeth
authors.forename: Mayumi
authors.initials: M
authors.lastname: Ohnishi-Kameyama
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Yoshida
authors.forename: Kozo
authors.initials: K
authors.lastname: Ochi
authors.forename: Gregory L
authors.initials: GL
authors.lastname: Challis
mesh_terms: D006877:Hydroxamic Acids / Q000737:chemistry* / Q000302:isolation & purification; D007502:Iron Chelating Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D008958:Models, Molecular; D008968:Molecular Conformation; D005810:Multigene Family / Q000235:genetics; D009842:Oligopeptides / Q000096:biosynthesis* / Q000737:chemistry* / Q000302:isolation & purification; D010453:Peptide Synthases / Q000235:genetics / Q000378:metabolism; D010944:Plants / Q000382:microbiology*; D017262:Siderophores / Q000096:biosynthesis* / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism; D013302:Streptomyces / Q000201:enzymology / Q000235:genetics / Q000378:metabolism*
chemical_list: D006877:Hydroxamic Acids; D007502:Iron Chelating Agents; D009842:Oligopeptides; D017262:Siderophores; C586156:scabichelin; D010453:Peptide Synthases