The Library
Structure and biosynthesis of scabichelin, a novel tris-hydroxamate siderophore produced by the plant pathogen Streptomyces scabies 87.22
Tools
Tools
Tools
Kodani, Shinya, Bicz, Joanna, Song, Lijiang, Deeth, Robert J., Ohnishi-Kameyama, Mayumi, Yoshida, Mitsuru, Ochi, Kozo and Challis, Gregory L. (2013) Structure and biosynthesis of scabichelin, a novel tris-hydroxamate siderophore produced by the plant pathogen Streptomyces scabies 87.22. Organic & Biomolecular Chemistry, Volume 11 (Number 28). pp. 4686-4694. doi:10.1039/c3ob40536b ISSN 1477-0520.
Research output not available from this repository.
Request-a-Copy directly from author or use local Library Get it For Me service.
Official URL: http://dx.doi.org/10.1039/c3ob40536b
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.
| Item Type: | Journal Article | ||||
|---|---|---|---|---|---|
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
| Journal or Publication Title: | Organic & Biomolecular Chemistry | ||||
| Publisher: | Royal Society of Chemistry | ||||
| ISSN: | 1477-0520 | ||||
| Official Date: | 11 June 2013 | ||||
| Dates: |
|
||||
| Volume: | Volume 11 | ||||
| Number: | Number 28 | ||||
| Page Range: | pp. 4686-4694 | ||||
| DOI: | 10.1039/c3ob40536b | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access |
Request changes or add full text files to a record
Repository staff actions (login required)
 |
View Item |
