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Novel bioactive lipodepsipeptides from Pseudomonas syringae : The pseudomycins
Author(s) -
Ballio A.,
Bossa F.,
Di Giorgio D.,
Ferranti P.,
Paci M.,
Pucci P.,
Scaloni A.,
Segre A.,
Strobel G.A.
Publication year - 1994
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(94)01179-6
Subject(s) - pseudomonas syringae , moiety , stereochemistry , chemistry , mutant , peptide , pseudomonas , strain (injury) , covalent bond , bacteria , biochemistry , biology , organic chemistry , genetics , anatomy , gene
The covalent structure and most of the stereochemistry of the pseudomycins, bioactive metabolites of a transposon‐generated mutant of a Pseudomonas syringae wild‐type strain proposed for the biological control of Dutch elm disease, have been determined. While two pseudomycins are identical to the known syringopeptins 25‐A and 25‐B, pseudomycins A, B, C, C′ are new lipodepsinonapeptides. For all of these the peptide moiety corresponds to l ‐Ser‐ d ‐Dab‐ l ‐Asp‐ l ‐Lys‐ l ‐Dab‐ l ‐aThr‐Z‐Dhb‐ l ‐Asp(3‐OH) ‐ l ‐Thr(4‐Cl) with the terminal carboxyl group closing a macrocyclic ring on the OH group of the N‐terminal Ser. This is in turn N ‐acylated by 3,4‐dihydroxytetradecanoate in pseudomycin A, by 3‐hydroxytetradecanoate in pseudomycin B, by 3,4‐dihydroxyhexadecanoate in pseudomycin C, and by 3‐hydroxyhexadecanoate in pseudomycin C′. Some preliminary data on the biological activity of pseudomycin A are reported.