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 spectroscopy NMR spectroscopy and chemical and enzymatic procedures allowed one to define a peptide moiety corresponding to Z-Dhb-D-Pro-L-Leu-D-Ala-D-Ala-D-Ala-D-Ala-D-Val-Gly-D-Ala-D-Val-D-Ala-D- Val-Z-Dhb-Da-Thr-L-Ala-L-Dab-D-Dab-L-Phe 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.
Ballio
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Dipartimento di Scienze Biochimiche 'A. Rossi Fanelli' e Centro di Biologia Molecolare del CNR, Università 'La Sapienza', Roma, Italy.
Bossa
F
F
Camoni
L
L
Di Giorgio
D
D
Flamand
M C
MC
Maraite
H
H
Nitti
G
G
Pucci
P
P
Scaloni
A
A
D000595:Amino Acid Sequence; D001426:Bacterial Proteins / Q000494:pharmacology; D001427:Bacterial Toxins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D010935:Plant Diseases / Q000382:microbiology; D011549:Pseudomonas / Q000378:metabolism*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013329:Structure-Activity Relationship
D001426:Bacterial Proteins; D001427:Bacterial Toxins; D010456:Peptides, Cyclic; C098810:fuscopeptin A; C098811:fuscopeptin B; C032677:syringomycin