Novel bioactive lipodepsipeptides from Pseudomonas syringae: the pseudomycins.

Abstract:

: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.

journal_name

FEBS Lett

journal_title

FEBS letters

authors

Ballio A,Bossa F,Di Giorgio D,Ferranti P,Paci M,Pucci P,Scaloni A,Segre A,Strobel GA

doi

10.1016/0014-5793(94)01179-6

subject

Has Abstract

pub_date

1994-11-21 00:00:00

pages

96-100

issue

1

eissn

0014-5793

issn

1873-3468

pii

0014-5793(94)01179-6

journal_volume

355

pub_type

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