Chemical Mediators:  The Remarkable Structure and Host-Selectivity of Depsilairdin, a Sesquiterpenic Depsipeptide Containing a New Amino Acid

The chemical structure determination of depsilairdin, a highly selective phytotoxin produced by the plant pathogenic fungus Leptosphaeria maculans/Phoma lingam, is described. The elucidation of the unusual chemical structure used a combination of NMR spectral data and X-ray crystallography. The abso...

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Published inOrganic letters Vol. 6; no. 24; pp. 4615 - 4617
Main Authors Pedras, M. Soledade C, Chumala, Paulos B, Quail, J. Wilson
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.11.2004
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Depsipeptides - chemistry
Depsipeptides - pharmacology
Mustard Plant - drug effects
Mycotoxins - chemistry
Mycotoxins - pharmacology
Physical Sciences
Plant Diseases - etiology
Plant Leaves - drug effects
Science & Technology
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
BLACKLEG FUNGUS
PHYTOTOXINS
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Summary:The chemical structure determination of depsilairdin, a highly selective phytotoxin produced by the plant pathogenic fungus Leptosphaeria maculans/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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0478786