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Structure of fuscopeptins, phytotoxic metabolites of Pseudomonas fuscovaginae
Author(s) -
Ballio A.,
Bossa F.,
Camoni L.,
Di Giorgio D.,
Flamand M.-C.,
Maraite H.,
Nitti G.,
Pucci P.,
Scaloni A.
Publication year - 1996
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(96)00043-9
Subject(s) - residue (chemistry) , moiety , chemistry , stereochemistry , pseudomonas , chemical structure , peptide , nuclear magnetic resonance spectroscopy , mass spectrometry , organic chemistry , biochemistry , bacteria , biology , chromatography , genetics
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 allo threonine 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.