Pyoverdine

Pyoverdine

Other names Pyoverdin
Identifiers
PubChem	45479427
Jmol-3D images	Image 1
SMILES CC(C1C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN(C=O)O)NC(=O)C(CCCN(C=O)O)NC(=O)C(CO)NC(=O)C(CCCN=C(N)N)NC(=O)C(CO)NC(=O)C2CCNC3N2C4=CC(=C(C=C4C=C3NC(=O)CCC(C(=O)O)N)O)O)C(C)O)O
Properties
Molecular formula	C₅₆H₈₈N₁₈O₂₂
Molar mass	1365.41 g mol⁻¹
Appearance	Solid
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 involed 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 exeption 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

^ 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.
^ 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
^ ^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