Syringopeptins, new phytotoxic lipodepsipeptides of Pseudomonas syringae pv. syringae

Abstract

The primary structure of some new lipodepsipeptides named syringopeptins, produced by plant pathogenic strains of Pseudomonas syringae pv. syringae has been determined by a combination of chemical methods, 1H and 13C NMR spectroscopy and FAB mass spectrometry. Two syringomycin-producing strains afforded 3-hydroxydecanoyl-Dhb-Pro-Val-Val-Ala-Ala-Val-Val-Dhb-Ala-Val-Ala- Ala-Dhb-aThr-Ser-Ala-Dhb-Ala-Dab-Dab-Tyr, with Tyr acylating a Thr to form a macrolactone ring, and smaller amounts of the 3-hydroxydodecanoyl homologue. Evidence was obtained that a third syringomycin-producing strain and a syringotoxin-producing strain synthesize 3-hydroxydecanoyl-Dhb-Pro-Val-Ala-Ala-Val-Leu-Ala-Ala-Dhb-Val-Dhb- Ala-Val-Ala-Ala-Dhb-aThr-Ser-Ala-Val-Ala-Dab-Dab-Tyr, with Tyr and aThr forming again the macrolactone ring, and smaller amounts of the 3-hydroxydodecanoyl homologue.