Structure and characterization of isopyoverdin from Pseudomonas putida BTP1 and its relation to the biogenetic pathway leading to pyoverdins

Z Naturforsch C J Biosci. Sep-Oct 1995;50(9-10):622-9. doi: 10.1515/znc-1995-9-1005.

Abstract

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-3H-pyrimido[1,2a]quinoline-3- carboxylic acid). The amino group of the chromophore is substituted with the 5-carboxyl group of L-glutamic acid and its carboxyl group with the N-terminus of the peptide L-Asp-L-Ala-L-Asp-D-N5-Ac-N5-OH-Orn-L-Ser-L-c-N5-OH-Orn. This isopyoverdin fits into the biogenetic scheme which postulates ferribactins as the precursors of pyoverdins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / analysis
  • Biotransformation
  • Isoelectric Focusing
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Oligopeptides / chemistry*
  • Oligopeptides / isolation & purification
  • Oligopeptides / metabolism*
  • Pigments, Biological / biosynthesis*
  • Pseudomonas putida / growth & development
  • Pseudomonas putida / metabolism*
  • Siderophores
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Amino Acids
  • Oligopeptides
  • Pigments, Biological
  • Siderophores
  • isopyoverdin
  • pyoverdin