Chemical mediators: The remarkable structure and host-selectivity of depsilairdin, a sesquiterpenic depsipeptide containing a new amino acid

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4615-4617

  Pedras, M Soledade C ^a   Chumala, Paulos B ^a   Wilson Quail, J ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BIOLOGICAL MARKER; DEPSILAIRDIN; DEPSIPEPTIDE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG; VEGETABLE PROTEIN;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL STRUCTURE; DEGRADATION KINETICS; FUNGAL PLANT DISEASE; FUNGAL VIRULENCE; HOST RANGE; HOST SELECTION; LEPTOSPIRA; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOCHEMISTRY; PLANT DISEASE; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

DEPSIPEPTIDES; MUSTARD PLANT; MYCOTOXINS; PLANT DISEASES; PLANT LEAVES; SESQUITERPENES;

EID: 10044280503     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0478786     Document Type: Article

References (21)

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11. Isolates producing sirodesmins (2) are classified as group A, but the new isolates Laird 2 and Mayfair 2 remain unclassified, cf. ref 3.
12. Compound 7 was crystallized from hexane-acetone (7:3). An X-ray crystallographic data file (CIF) can be found in Supporting Information.
13. 3-OD. After completion of the reaction (15 days), the reaction mixture was concentrated to dryness and the residue separated by chromatography.
14. H 4.52.
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19. Bioassays described in Supporting Information, as previously reported for other toxins: Pedras, M. S. C.; Biesenthal, C. J.; Zaharia, I. L. Plant Sci. 2000, 156, 185-192.
20. -3 M. For a multiauthor review on phytotoxins, see: Graniti, A. Experientia 1991, 47, 751-755.
21. We suspect that blackleg isolates similar to Mayfair 2 and Laird 2 are not common because their favorite host is not widely cultivated. Nonetheless, because new oilseed varieties of brown mustard are commercially available, the new blackleg type may soon become widespread.