Monatshefte für Chemie / Chemical Monthly

, Volume 123, Issue 1, pp 151–178

Neue Siderophore des Pyoverdin-Typs ausPseudomonas fluorescens

Authors

  • Karl Geisen
    • Institut für Organische ChemieUniversität Köln
  • Kambiz Taraz
    • Institut für Organische ChemieUniversität Köln
  • Herbert Budzikiewicz
    • Institut für Organische ChemieUniversität Köln
Organische Chemie Und Biochemie

DOI: 10.1007/BF01045308

Cite this article as:
Geisen, K., Taraz, K. & Budzikiewicz, H. Monatsh Chem (1992) 123: 151. doi:10.1007/BF01045308

Verwendete Abkürzungen

ASK

Acylseitenkette

Chr

Chromophor1 a

(HO)Chr

Chromophor1 b

Dns

Dansyl-Rest

DP

Dansylpeptid

EDTA

Ethylendiamintetraessigsäure

FAB

Fast Atom Bombardment (PI=positive Ionen)

(HO)Orn

N5-Hydroxyornithin

(CHO, HO)Orn

N5-Formyl-N5-hydroxyornithin

PITC

Phenylisothiocyanat

RP-HPLC

Reversed-Phase High Performance Liquid Chromatography

Kgl

α-Ketoglutarsäure bzw. 4-Carboxy-4-oxobutanoyl-Rest

R t

Retentionszeit

Suc

Bernsteinsäure bzw. 3-Carboxypropanoyl-Rest

Suca

Succinamoyl-Rest

Suci

Succinimido-Rest

TAB

Trifluoracetyl-n-butylester

TEA

Triethylamin

New pyoverdin type siderophores fromPseudomonas fluorescens

Summary

The structure of four new pyoverdins (Pf12-IA, -IIA, -IB und IIB) isolated from the culture medium ofPseudomonas fluorescens 12 was elucidated by combination of spectroscopic methods and degradation reactions. The pyoverdins comprise (1S)-5-amino-2,3-dihydro-8,9-dihydroxy-1H-pyrimido[1,2-a]quinoline-1-carboxylic acid whose amino group carries a 3-carboxypropanoyl-(IA), succinamoyl- (IIA), 4-carboxy-4-oxobutanoyl- (IB) or L-4-amino-4-carboxybutanoylresidue (II B) and whose carboxyl group is bound amidically to the N-terminus of D-Ser-L-Lys-Gly-
. According to the short-hand-nomenclature suggested in [2, 3] the pyoverdins may be described as pyoverdin-Q-sKGO′sSGK*o′ES*-SUC(IA), pyoverdin-Q-sKGO′sSGK*o′-ES*-SUCA (IIA), pyoverdin-Q-sKGO′sSGK*o′ES*-KGL (IB) and pyoverdin-Q-sKGO′sSGK*o′ES*-GLU (IIB). The pyoverdins described here possess the most complex structure encountered so far as their peptide part comprises eleven amino acids and the cyclo-tetrapeptide substructure. In addition, they are of special interest as for the first time glutamic acid could be identified as a chromophore side chain which is the key compound for the citric acid cycle to which belong all dicarboxylic acids found so far in pyoverdins.

Keywords

Citric acid cycle Pseudomonas fluorescens Pyoverdins Siderophores Structure elucidation

Copyright information

© Springer-Verlag 1992