Pyoverdine

Pyoverdine

Names
Other names Pyoverdin
Identifiers
Jmol interactive 3D	Image
PubChem	45479427
InChI Key: QIRRYPHVUMPBDX-UARRTFJPSA-N
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
Chemical formula	C56H88N18O22
Molar mass	1,365.42 g·mol^−1
Appearance	Solid
Except where otherwise noted, 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) are fluorescent siderophores produced by certain pseudomonad bacteria species.^[1][2]

In Pseudomonas aeruginosa PAO1 there are 14 pvd genes involved in the biosynthesis of pyoverdine.^[3]

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.^[4]

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^[4]

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

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. Menhart, N., Thariath, A., Viswanatha, T. (1991) Characterization of the pyoverdines of Azotobacter vinelandii ATCC 12837 with regard to heterogeneity. Biology of Metals 4(4):223-32
3. 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.
4. 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.