title: Chemical mediators: the remarkable structure and host-selectivity of depsilairdin, a sesquiterpenic depsipeptide containing a new amino acid.
abstract: The chemical structure determination of depsilairdin, a highly selective phytotoxin produced by the plant pathogenic fungus Leptosphaeriamaculans/Phoma lingam, is described. The elucidation of the unusual chemical structure used a combination of NMR spectral data and X-ray crystallography. The absolute configuration was established using chemical degradation and synthesis of (3S,6R)-3,6-diisopropyl-2,5-morpholinedione and its (3R,6S) and (3R,6R) stereoisomers. Similar to the fungal pathogen, depsilairdin caused strong lesions only on brown mustard leaves but not on related species. [structure: see text]
authors.affiliation: Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, Saskatchewan S7N 5C9, Canada. s.pedras@usask.ca
authors.forename: M Soledade C
authors.initials: MS
authors.lastname: Pedras
authors.forename: Paulos B
authors.initials: PB
authors.lastname: Chumala
authors.forename: J Wilson
authors.initials: JW
authors.lastname: Quail
mesh_terms: D047630:Depsipeptides / Q000737:chemistry* / Q000494:pharmacology; D009149:Mustard Plant / Q000187:drug effects; D009183:Mycotoxins / Q000737:chemistry* / Q000494:pharmacology; D010935:Plant Diseases / Q000209:etiology; D018515:Plant Leaves / Q000187:drug effects; D012717:Sesquiterpenes / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D047630:Depsipeptides; D009183:Mycotoxins; D012717:Sesquiterpenes; C507168:depsilairdin