Pyoverdin type siderophores produced by six fluorescent Pseudomonas strains isolated from different rhizospheres were purified and characterized. The purified ferri-pyoverdins were tested for their ability to promote the growth of other strains grown under iron deficiency conditions. Only the one obtained from Pseudomonas putida BTP1 did not act as a growth promoter.
The structure of the BTP1 siderophore was elucidated by spectroscopic methods and degradation studies. It turned out that it contains a chromophore which differs from the one typical for pyoverdins insofar as it carries the carboxyl group in 3- rather than in 1-position ((3S)-5-amino-1,2-dihydro-8,9-dihydroxy-3 H -pyrimido[1,2 a]quinoline-3-carboxylic acid). The amino group of the chromophore is substituted with the 5-carboxyl group of ʟ-glutamic acid and its carboxyl group with the N -terminus of the peptide ʟ -A sp -ʟ -A la-ʟ -Asp - ᴅ-N5- Ac - N5- OH - Orn - ʟ - Ser - ʟ - ᴄ - N5- OH - Orn . This isopyoverdin fits into the biogenetic scheme which postulates ferribactins as the precursors of pyoverdins
New Pyoverdin Siderophores from Pseudomonas putida C
Four new pyoverdins (C 2A, C 2B, C 3A, C 3B) 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‐ (C 2A), succinamoyl‐ (C 2B), L‐3‐carboxy‐2‐hydroxypropanoyl‐ (C 3A) or 3‐carboxypropanoyl (C 3B) 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.
Pseudomonas fluorescens, Siderophores, Pyoverdins, Pseudobactin, Structure Elucidation From a strain of Pseudomonas fluorescens pseudobactin and several related compounds were isolated and their structures were elucidated. In this way a reference compound (5) could be obtained for the unambiguous determination of the absolute configuration of C-l of the pyoverdin chromophore in newly isolated representatives of this class.
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