Structure of fuscopeptins, phytotoxic metabolites of Pseudomonas fuscovaginae

The structure of the fuscopeptins, bioactive lipodepsipeptides produced in culture by the gramineae pathogen Pseudomonas fuscovaginae, has been determined. The combined use of FAB mass spectrometry, NMR spectroscopy and chemical and enzymatic procedures allowed one to define a peptide moiety corresp...

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Veröffentlicht in:	FEBS letters 1996-03, Vol.381 (3), p.213-216
Hauptverfasser:	Ballio, A., Bossa, F., Camoni, L., Di Giorgio, D., Flamand, M.-C., Maraite, H., Nitti, G., Pucci, P., Scaloni, A.
Format:	Artikel
Sprache:	eng
Schlagworte:	Amino Acid Sequence aThr, allothreonine Bacterial Proteins - pharmacology Bacterial Toxins - chemistry Bacterial Toxins - isolation & purification Bacterial Toxins - pharmacology Dab, 2,4-diaminobutyric acid Dhb, 2,3-dehydro-2-aminobutyric acid FAB-MS, fast atom bombardment mass spectrometry FP, fuscopeptin Fungi - drug effects Fuscopeptins GC-MS, gas chromatography mass spectrometry Lipodepsipeptides Magnetic Resonance Spectroscopy Microbial Sensitivity Tests Molecular Sequence Data Peptides, Cyclic - chemistry Peptides, Cyclic - isolation & purification Peptides, Cyclic - pharmacology Phytotoxins Plant Diseases - microbiology Pseudomonas - metabolism Pseudomonas fuscovaginae SP, syringopeptin Spectrometry, Mass, Fast Atom Bombardment SR, syringomycin Structure-Activity Relationship TBDMS, t-butyldimethylsilyl TFA, trifluoroacetic acid
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Beschreibung
Zusammenfassung:	The structure of the fuscopeptins, bioactive lipodepsipeptides produced in culture by the gramineae pathogen Pseudomonas fuscovaginae, has been determined. The combined use of FAB mass spectrometry, NMR spectroscopy and chemical and enzymatic procedures allowed one to define a peptide moiety corresponding to ZDhb-DPro-LLeu-DAla-DAla-DAla-DAlaDVal-Gly-DAla-DVal-DAla-DVal-ZDhb-DaThr-LAla-LDabDDab-LPhe with the terminal carboxyl group closing a macrocyclic ring on the hydroxyl group of the allothreonine residue. The N-terminus is in turn acylated by 3-hydroxyoctanoate in fuscopeptin A and 3-hydroxydecanoate in fuscopeptin B. Some preliminary data on the biological activity of fuscopeptins are also reported.
ISSN:	0014-5793 1873-3468
DOI:	10.1016/0014-5793(96)00043-9