Pyoverdine

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Pyoverdine
Pyoverdine.svg
Identifiers
PubChem 45479427
Jmol-3D images Image 1
Properties
Molecular formula C56H88N18O22
Molar mass 1,365.41 g mol−1
Appearance Solid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Pyoverdine (or pyoverdin) is a fluorescent siderophore produced by the Gram negative bacterium Pseudomonas aeruginosa.[1]

In Pseudomonas aeruginosa PAO1 there are 14 pvd genes involved in the synthesis of the pyoveridine.[2]

Unlike Enterobactin, Pyoverdine/pseudobactins are iron-binding non-ribosomal peptides containing a dihydroxyquinoline derivative. The structure of the peptide differs between pseudomonads and over 40 structures have been described, while the chromophore, (1S)-5-amino-2,3-dihydro- 8,9-dihydroxy-1H-pyrimido[1,2-a]quinoline-1-carboxylic acid, is the same with the exception of azobactin from Azotobacter vinelandii, which possesses an extra urea ring.[3]

Structure of the peptide backbone in various fluorescent Pseudomonas strains. Amino acid three-letter code are used along with Q=chromophore, DXxx=D amino acid, aThr=allo-threonine, c=cyclic structure, cOHOrn=cyclo-hydroxyornithine, Dab=diaminobutyric acid, Ac=Acetyl, Fo=formyl OH=hydroxyl[3]
Pseudomonad species Strain Structure of the pyoverdine peptide chain
P. aeruginosa ATCC15692 Q-DSer-Arg-DSer-FoOHOrn-c(Lys-FoOHOrn-Thr-Thr)
P. aeruginosa ATCC27853 Q-DSer-FoOHDOrn-Orn-Gly-aDThr-Ser-cOHOrn
P. aeruginosa Pa6 Q-DSer-Dab-FoOHOrn-Gln-DGln-FoOHDOrn-Gly
P. chlororaphis ATCC9446 Q-DSer-Lys-Gly-FoOHOrn-c(Lys-FoOHDOrn-Ser)
P. fluorescens bv.I ATCC13525 Q-DSer-Lys-Gly-FoOHOrn-c(Lys-FoOHDOrn-Ser)
P. fluorescens bv.I 9AW Q-DSer-Lys-OHHis-aDThr-Ser-cOHOrn
P. fluorescens bv.III ATCC17400 Q-DAla-DLys-Gly-Gly-OHAsp-DGln/Dab-Ser-DAla-cOHOrn
P. fluorescens bv.V 51W Q-DAla-DLys-Gly-Gly-OHDAsp-DGln-DSer-Ala-Gly-aDThr-cOHOrn
P. fluorescens bv.V 1W Q-DSer-Lys-Gly-FoOHOrn-c(Lys-FoOHDOrn-Ser)
P. fluorescens bv.V 10CW Q-DSer-Lys-Gly-FoOHOrn-c(Lys-FoOHDOrn-Ser)
P. fluorescens bv.VI PL7 Q-DSer-AcOHDOrn-Ala-Gly-aDThr-Ala-cOHOrn
P. fluorescens bv.VI PL8 Q-DLys-AcOHDOrn-Ala-Gly-aDThr-Ser-cOHOrn
P. fluorescens 1.3 Q-DAla-DLys-Gly-Gly-OHAsp-DGln/Dab-Gly-Ser-cOHOrn
P. fluorescens 18.1 Q-DSer-Lys-Gly-FoOHOrn-Ser-DSer-Gly-c(Lys-FoOHDOrn-Ser)
P. fluorescens CCM 2798 Q-Ser-Dab-Gly-Ser-OHDAsp-Ala-Gly-DAla-Gly-cOHOrn
P. fluorescens CFBP 2392 Q-DLys-AcOHDOrn-Gly-aDThr-Thr-Gln-Gly-DSer-cOHOrn
P. fluorescens CHA0 Q-Asp-FoOHDOrn-Lys-c(Thr-Ala-Ala-FoOHDOrn-Lys)
P. putida bv. B 9BW Q-DSer-Lys-OHHis-aDThr-Ser-cOHOrn
P. putida CFBP 2461 Q-Asp-Lys-OHDAsp-Ser-aDThr-Ala-Thr-DLys-cOHOrn
P. tolaasii NCPPB 2192 Q-DSer-Lys-Ser-DSer-Thr-Ser-AcOHOrn-Thr-DSer-cOHDOrn

References[edit]

  1. ^ S. Wendenbaum, P. Demange, A. Dell, J. M. Meyer and M. A. Abdallah (1983). "The structure of pyoverdine Pa, the siderophore of Pseudomonas aeruginosa". Tetrahedron Letters 24 (44): 4877–4880. doi:10.1016/S0040-4039(00)94031-0. 
  2. ^ Lamont, I. L.; Martin, L. W. (2003). "Identification and characterization of novel pyoverdine synthesis genes in Pseudomonas aeruginosa". Microbiology 149 (4): 833. doi:10.1099/mic.0.26085-0.  edit
  3. ^ a b Meyer, J. M. (2000). "Pyoverdines: Pigments, siderophores and potential taxonomic markers of fluorescent Pseudomonas species". Archives of Microbiology 174 (3): 135–142. doi:10.1007/s002030000188. PMID 11041343.  edit