Neue Pyoverdin-Siderophore ausPseudomonas putida C

Journal f�r Praktische Chemie/Chemiker-Zeitung
1993.0

Abstract

Four new pyoverdins (C2A, C2B, C3A, C3B) were isolated from cultures of Pseudomonas putida C. Their structures were elucidated by chemical and spectroscopic methods. The compounds consist of a chromophore - (1S)-5-amino-2,3-dihydro-8,9-dihydroxy-1H-pyrimido[1,2-a]quinoline-1-carboxylic acid - substituted at the amino group with a dicarboxylic acid or its amide. The carboxyl group of the chromophore is amidically bound to the N-terminus of L-Asp-D-[N5-hydroxy-N5-(D-β-hydroxybutyryl)]Orn-D-Dab-L-Thr-Gly-D-Ser-L-Ser-L-threo-β-hydroxy-Asp-L-Thr. The four pyoverdins differ only in the nature of the dicarboxylic acid (amide), viz. L-malamoyl- (C2A), succinamoyl- (C2B), L-3-carboxy-2-hydroxypropanoyl- (C3A) or 3-carboxypropanoyl (C3B) residue. The hydroxamate function consists of N5-hydroxy-Orn and β-hydroxybutyric acid, a structural unit which has been encountered for the first time in a pyoverdin.

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