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Neue Siderophore des Pyoverdin-Typs ausPseudomonas fluorescens

New pyoverdin type siderophores fromPseudomonas fluorescens

  • Organische Chemie Und Biochemie
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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.

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Abbreviations

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

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Geisen, K., Taraz, K. & Budzikiewicz, H. Neue Siderophore des Pyoverdin-Typs ausPseudomonas fluorescens . Monatsh Chem 123, 151–178 (1992). https://doi.org/10.1007/BF01045308

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