Pyoverdine

Structural formula of pyoverdin C , CAS number: 104022-78-8, molecular formula C ₅₆ H ₈₈ N ₁₈ O ₂₂

The Pyoverdine are a group of currently 60 known fluorescent siderophores and oligopeptide - antibiotics caused by the gram-negative bacteria Pseudomonas aeruginosa and Pseudomonas fluorescens produced.

Pyoverdine serve pseudomonas the induction of virulence factors . Pyoverdines are divided into three types, each pseudomonad strain only produces one type. In Pseudomonas aeruginosa PAO1, 14 pvd genes are involved in the synthesis of pyoveridines.

In contrast to enterobactins , pyoverdines are iron-binding , non-ribosomal peptides that contain a dihydroxyquinoline derivative. The structure of the peptides differs between different pseudomonads and more than 40 structures have been described. The actual chromophore (1 S ) -5-amino-2,3-dihydro-8,9-dihydroxy-1 H -pyrimido [1,2- a ] -quinoline-1-carboxylic acid, on the other hand, is the same, with the exception of azobactin from Azotobacter vinelandii , which contains another urea ring.

Structure of the peptide backbone of various pseudomonads.
Pseudomonad species	tribe	Structure of the peptide chain of pyoverdin
The amino acid three-letter code is together with the abbreviations Q = chromophore, Dxxx = D- amino acid , aThr = allo-threonine , c = cyclic structure, cOHOrn = cyclo-hydroxyornithine , Dab = diamino butyric acid , Ac = acetyl group , Fo = formyl group, OH = hydroxy group , OHAsn = β-hydroxyaspartic acid listed.
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
P. taiwanensis	VLB120	Q-Orn-Asp-OHAsn-Thr-AcOHOrn-Ser-cOHOrn

Individual evidence

^ ^A ^b I. J. Schalk, L. Guillon: Pyoverdine biosynthesis and secretion in Pseudomonas aeruginosa: implications for metal homeostasis. In: Environ Microbiol. (2013), Volume 15, No. 6, pp. 1661–1673. doi : 10.1111 / 1462-2920.12013 . PMID 23126435 .
↑ S. Wendenbaum, P. Demange, A. Dell, JM Meyer and MA Abdallah: The structure of pyoverdine Pa, the siderophore of Pseudomonas aeruginosa . In: Tetrahedron Letters . 24, No. 44, 1983, pp. 4877-4880. doi : 10.1016 / S0040-4039 (00) 94031-0 .
↑ Entry on pyoverdine. In: Römpp Online . Georg Thieme Verlag, accessed on August 2, 2013.
↑ ^a ^b P. N. Jimenez, G. Koch, JA Thompson, KB Xavier, RH Cool, WJ Quax: The multiple signaling systems regulating virulence in Pseudomonas aeruginosa. In: Microbiol Mol Biol Rev. (2012), Vol. 76, No. 1, pp. 46-65. doi : 10.1128 / MMBR.05007-11 . PMID 22390972 ; PMC 3294424 (free full text).
↑ IL Lamont, LW Martin: Identification and characterization of novel pyoverdine synthesis genes in Pseudomonas aeruginosa . In: Microbiology . 149, 2003, p. 833. doi : 10.1099 / mic.0.26085-0 .
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u J. M. Meyer: Pyoverdines: Pigments, siderophores and potential taxonomic markers of fluorescent Pseudomonas species . In: Archives of Microbiology . 174, 2000, pp. 135-142. doi : 10.1007 / s002030000188 .
↑ M. Baune, Y. Qi, K. Scholz, D. Vollmer, H. Hayen: Structural Characterization of Pyoverdines Produced by Pseudomonas Putida KT2440 and Pseudomonas Taiwanensis VLB120 . In: BioMetals . 30, 2017, pp. 589-597. doi : 10.1007 / s10534-017-0029-7 .

[Schalk-1] A ^b I. J. Schalk, L. Guillon: Pyoverdine biosynthesis and secretion in Pseudomonas aeruginosa: implications for metal homeostasis. In: Environ Microbiol. (2013), Volume 15, No. 6, pp. 1661–1673. doi : 10.1111 / 1462-2920.12013 . PMID 23126435 .

[2] S. Wendenbaum, P. Demange, A. Dell, JM Meyer and MA Abdallah: The structure of pyoverdine Pa, the siderophore of Pseudomonas aeruginosa . In: Tetrahedron Letters . 24, No. 44, 1983, pp. 4877-4880. doi : 10.1016 / S0040-4039 (00) 94031-0 .

[roempp-3] Entry on pyoverdine. In: Römpp Online . Georg Thieme Verlag, accessed on August 2, 2013.

[Jimenez-4] P. N. Jimenez, G. Koch, JA Thompson, KB Xavier, RH Cool, WJ Quax: The multiple signaling systems regulating virulence in Pseudomonas aeruginosa. In: Microbiol Mol Biol Rev. (2012), Vol. 76, No. 1, pp. 46-65. doi : 10.1128 / MMBR.05007-11 . PMID 22390972 ; PMC 3294424 (free full text).

[5] IL Lamont, LW Martin: Identification and characterization of novel pyoverdine synthesis genes in Pseudomonas aeruginosa . In: Microbiology . 149, 2003, p. 833. doi : 10.1099 / mic.0.26085-0 .

[structure-6] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u J. M. Meyer: Pyoverdines: Pigments, siderophores and potential taxonomic markers of fluorescent Pseudomonas species . In: Archives of Microbiology . 174, 2000, pp. 135-142. doi : 10.1007 / s002030000188 .

[7] M. Baune, Y. Qi, K. Scholz, D. Vollmer, H. Hayen: Structural Characterization of Pyoverdines Produced by Pseudomonas Putida KT2440 and Pseudomonas Taiwanensis VLB120 . In: BioMetals . 30, 2017, pp. 589-597. doi : 10.1007 / s10534-017-0029-7 .