Iron acquisition with the natural siderophore enantiomers pyochelin and enantio-pyochelin in Pseudomonas species

BioMetals

Volumn 24, Issue 3, 2011, Pages 513-522

  Youard, Zeb A ^a   Wenner, Nicolas ^a   Reimmann, Cornelia ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Enantio pyochelin; Enantiomer; Pseudomonas; Pyochelin; Siderophore; Stereospecificity

Indexed keywords

CARRIER PROTEIN; CYSTEINE; IRON; MEMBRANE RECEPTOR; PCHR PROTEIN; PYOCHELIN; REGULATOR PROTEIN; SALICYLIC ACID; SIDEROPHORE; THIAZOLINE; UNCLASSIFIED DRUG;

BACTERIAL GROWTH; BIOSYNTHESIS; CONFERENCE PAPER; CYTOSOL; ENANTIOMER; GENE EXPRESSION; IRON TRANSPORT; METHYLATION; NONHUMAN; PROTEIN FUNCTION; PROTEIN STRUCTURE; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA; PSEUDOMONAS FLUORESCENS; STEREOCHEMISTRY; STEREOSPECIFICITY; TRANSCRIPTION REGULATION;

AMINO ACID SEQUENCE; IRON; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHENOLS; PSEUDOMONAS; SEQUENCE ALIGNMENT; SIDEROPHORES; STEREOISOMERISM; THIAZOLES;

BACTERIA (MICROORGANISMS); PSEUDOMONAS; PSEUDOMONAS AERUGINOSA; PSEUDOMONAS FLUORESCENS;

EID: 79959940464     PISSN: 09660844     EISSN: 15728773     Source Type: Journal    
DOI: 10.1007/s10534-010-9399-9     Document Type: Conference Paper

References (61)

1. Andrews SC, Robinson AK, Rodríguez-Quiñones F (2003) Bacterial iron homeostasis. FEMS Microbiol Rev 27:215-237 (Pubitemid 36694657)
2. Ankenbauer RG, Quan HN (1994) FptA, the Fe(III)-pyochelin receptor of Pseudomonas aeruginosa: a phenolate siderophore receptor homologous to hydroxamate siderophore receptors. J Bacteriol 176:307-319 (Pubitemid 24034046)
3. Ankenbauer RG, Toyokuni T, Staley A, Rinehart KL Jr, Cox CD (1988) Synthesis and biological activity of pyochelin, a siderophore of Pseudomonas aeruginosa. J Bacteriol 170:5344-5351 (Pubitemid 18259469)
4. Bodilis J, Cornelis P (2009) A survey of TonB-dependent receptors in fluorescent pseudomonads. Environ Microbiol Rep 1:256-262
5. Braud A, Hannauer M, Mislin GLA, Schalk IJ (2009) The Pseudomonas aeruginosa pyochelin-iron uptake pathway and its metal specificity. J Bacteriol 191:3517-3525
6. Budzikiewicz H (2004) Siderophores of the Pseudomonadaceae sensu stricto (fluorescent and non-fluorescent Pseudomonas spp.). Fortschr Chem Org Naturst 87:81-237
7. Castignetti D (1997) Probing of Pseudomonas aeruginosa, Pseudomonas aureofaciens, Burkholderia (Pseudomonas) cepacia, Pseudomonas fluorescens, and Pseudomonas putida with the ferripyochelin receptor A gene and the synthesis of pyochelin in Pseudomonas aureofaciens, Pseudomonas fluorescens, and Pseudomonas putida. Curr Microbiol 34:250-257 (Pubitemid 27150367)
8. Cobessi D, Celia H, Pattus F (2005) Crystal structure at high resolution of ferric-pyochelin and its membrane receptor FptA from Pseudomonas aeruginosa. J Mol Biol 352:893-904 (Pubitemid 41267075)
9. Cornelis P (2010) Iron uptake and metabolism in pseudomonads. Appl Microbiol Biotechnol 86:1637-1645
10. Cox CD (1980) Iron uptake with ferripyochelin and ferric citrate by Pseudomonas aeruginosa. J Bacteriol 142:581-587 (Pubitemid 10044946)
11. Cox CD, Graham R (1979) Isolation of an iron-binding compound from Pseudomonas aeruginosa. J Bacteriol 137: 357-364 (Pubitemid 9097580)
12. Cox CD, Rinehart KL, Moore ML, Cook JC (1981) Pyochelin: novel structure of an iron-chelating growth promoter for Pseudomonas aeruginosa. Proc Natl Acad Sci USA 78:4256-4260
13. DeClue MS, Baldridge KK, Künzler DE, Kast P, Hilvert D (2005) Isochorismate pyruvate lyase: a pericyclic reaction mechanism? J Am Chem Soc 127:15002-15003 (Pubitemid 41547348)
14. Drechsel H, Jung G, Winkelmann G (1992) Stereochemical characterization of rhizoferrin and identification of its dehydration products. Biometals 5:141-148
15. Escolar L, Perez-Martin J, de Lorenzo V (1999) Opening the iron box: transcriptional metalloregulation by the Fur protein. J Bacteriol 181:6223-6229 (Pubitemid 29512928)
16. Gaille C, Kast P, Haas D (2002) Salicylate biosynthesis in Pseudomonas aeruginosa. J Biol Chem 277:21768-21775
17. Gaille C, Reimmann C, Haas D (2003) Isochorismate synthase (PchA), the first and rate-limiting enzyme in salicylate biosynthesis of Pseudomonas aeruginosa. J Biol Chem 278:16893-16898 (Pubitemid 36799561)
18. Guerinot ML (1994) Microbioal iron transport. Annu Rev Microbiol 48:743-772
19. Harrison AJ, Yu M, Gárdenborg T, Middleditch M, Ramsay RJ, Baker EN, Lott JS (2006) The structure of MbtI from Mycobacterium tuberculosis, the first enzyme in the biosynthesis of the siderophore mycobactin, reveals it to be a salicylate synthase. J Bacteriol 188:6081-6091 (Pubitemid 44448550)
20. Hayen H, Volmer DA (2006) Different iron-chelating properties of pyochelin diastereoisomers revealed by LC/MS. Anal Bioanal Chem 385:606-611 (Pubitemid 43787459)
21. Heinrichs DE, Poole K (1993) Cloning and sequence analysis of a gene (pchR) encoding an AraC family activator of pyochelin and ferripyochelin receptor synthesis in Pseudomonas aeruginosa. J Bacteriol 175:5882-5889 (Pubitemid 23277436)
22. Heinrichs DE, Poole K (1996) PchR, a regulator of ferripyochelin receptor gene (fptA) expression in Pseudomonas aeruginosa, functions both as an activator and a repressor. J Bacteriol 178:2586-2592 (Pubitemid 26134483)
23. Hoegy F, Lee X, Noel S, Rognan D, Mislin GL, Reimmann C, Schalk IJ (2009) Stereospecificity of the siderophore pyochelin outer membrane transporters in fluorescent pseudomonads. J Biol Chem 284:14949-14957
24. Ino A, Murabayashi A (2001) Synthetic studies of thiazoline and thiazolidine-containing natural products. Part 3: total synthesis and absolute configuration of the siderophore yersiniabactin. Tetrahedron 57:1897-1902 (Pubitemid 32178516)
25. Kerbarh O, Ciulli A, Howard NI, Abell C (2005) Salicylate biosynthesis: overexpression, purification, and characterization of Irp9, a bifunctional salicylate synthase from Yersinia enterocolitica. J Bacteriol 187:5061-5066 (Pubitemid 41022922)
26. Kerbarh O, Chirgadze DY, Blundell TL, Abell C (2006) Crystal structures of Yersinia enterocolitica salicylate synthase and its complex with the reaction products salicylate and pyruvate. J Mol Biol 357:524-534 (Pubitemid 43290752)
27. Klumpp C, Burger A, Mislin GL, Abdallah MA (2005) From a total synthesis of cepabactin and its 3:1 ferric complex to the isolation of a 1:1:1 mixed complex between iron(III), cepabactin and pyochelin. Bioorg Med Chem Lett 15: 1721-1724 (Pubitemid 40312559)
28. Köster W (2001) ABC transporter-mediated uptake of iron, siderophores, heme and vitamin B12. Res Microbiol 152:291-301 (Pubitemid 32436487)
29. Künzler DE, Sasso S, Gamper M, Hilvert D, Kast P (2005) Mechanistic insights into the isochorismate pyruvatelyase activity of the catalytically promiscuous PchB from combinatorial mutagenesis and selection. J Biol Chem 280:32827-32834 (Pubitemid 41368330)
30. Liu PV, Shokrani F (1978) Biological activities of pyochelins: iron-chelating agents of Pseudomonas aeruginosa. Infect Immun 22:878-890 (Pubitemid 9083977)
31. Meyer J-M (2000) Pyoverdines: pigments, siderophores and potential taxonomic markers of fluorescent Pseudomonas species. Arch Microbiol 174:135-142
32. Michel L, Gonzalez N, Jagdeep S, Nguyen-Ngoc T, Reimmann C (2005) PchR-box recognition by the AraC-type regulator PchR of Pseudomonas aeruginosa requires the siderophore pyochelin as an effector. Mol Microbiol 58:495-509 (Pubitemid 41476164)
33. Michel L, Bachelard A, Reimmann C (2007) Ferripyochelin uptake genes are involved in pyochelin-mediated signalling in Pseudomonas aeruginosa. Microbiology 153: 1508-1518 (Pubitemid 46804321)
34. Münzinger M, Taraz K, Budzikiewicz H, Drechsel H, Heymann P, Winkelmann G, Meyer J-M (1999) S, S-rhizoferrin (enantio-rhizoferrin) - a siderophore of Ralstonia (Pseudomonas) pickettii DSM 6297 - the optical antipode of R, R-rhizoferrin isolated from fungi. Biometals 12: 189-193 (Pubitemid 29276801)
35. Namiranian S, Richardson DJ, Russell DA, Sodeau JR (1997) Excited state properties of the siderophore pyochelin and its complex with zinc ions. Photochem Photobiol 65: 777-782 (Pubitemid 27235790)
36. Ó Cuív P, Clarke P, Lynch D, O'Connell M (2004) Identification of rhtX and fptX, novel genes encoding proteins that show homology and function in the utilization of the siderophores rhizobactin 1021 by Sinorhizobium meliloti and pyochelin by Pseudomonas aeruginosa, respectively. J Bacteriol 186:2996-3005 (Pubitemid 38612853)
37. Ochsner UA, Vasil AI, Vasil ML (1995) Role of the ferric uptake regulator of Pseudomonas aeruginosa in the regulation of siderophores and exotoxin A expression: purification and activity on iron-regulated promoters. J Bacteriol 177:7194-7201
38. Patel HM, Walsh CT (2001) In vitro reconstitution of the Pseudomonas aeruginosa nonribosomal peptide synthesis of pyochelin: characterization of backbone tailoring thiazoline reductase and N-methyltransferase activities. Biochemistry 40:9023-9031 (Pubitemid 32709537)
39. Patel HM, Tao J, Walsh CT (2003) Epimerization of an L-cysteinyl to a D-cysteinyl residue during thiazoline ring formation in siderophore chain elongation by pyochelin synthetase from Pseudomonas aeruginosa. Biochemistry 42:10514-10527 (Pubitemid 37071452)
40. Paulsen IT, Press CM, Ravel J, Kobayashi DY, Myers GSA et al (2005) Complete genome sequence of the plant commensal Pseudomonas fluorescens Pf-5. Nat Biotechnol 23:873-878 (Pubitemid 43093131)
41. Pelludat C, Brem D, Heesemann J (2003) Irp9, encoded by the high-pathogenicity island of Yersinia enterocolitica, is able to convert chorismate into salicylate, the precursor of the siderophore yersiniabactin. J Bacteriol 185:5648-5653 (Pubitemid 37082423)
42. Quadri LEN, Keating TA, Patel HM, Walsh CT (1999) Assembly of the Pseudomonas aeruginosa nonribosomal peptide siderophore pyochelin: in vitro reconstitution of aryl-4, 2-bisthiazoline synthetase activity from PchD, PchE and PchF. Biochemistry 38:14941-14954
43. Reimmann C, Serino L, Beyeler M, Haas D (1998) Dihydroaeruginoic acid synthetase and pyochelin synthetase, products of the pchEF genes are induced by extracellular pyochelin in Pseudomonas aeruginosa. Microbiology 144:3135-3148 (Pubitemid 28515593)
44. Reimmann C, Patel HM, Serino L, Barone M, Walsh CT, Haas D (2001) Essential PchG-dependent reduction in pyochelin biosynthesis of Pseudomonas aeruginosa. J Bacteriol 183:813-820 (Pubitemid 32095289)
45. Reimmann C, Patel HM, Walsh CT, Haas D (2004) PchC thioesterase optimizes nonribosomal biosynthesis of the peptide siderophore pyochelin in Pseudomonas aeruginosa. J Bacteriol 186:6367-6373 (Pubitemid 39258117)
46. Rinehart KL, Staley AL, Wilson SR, Ankenbauer RG, Cox CD (1995) Stereochemical assignment of the pyochelins. J Org Chem 60:2786-2791
47. Schlegel K, Taraz K, Budzikiewicz H (2004) The stereoisomers of pyochelin, a siderophore of Pseudomonas aeruginosa. Biometals 17:409-414 (Pubitemid 38870175)
48. 3+ complex. Z Naturforsch 61c:263-266
49. Schmidli-Sacherer P, Keel C, Défago G (1997) The global regulator GacA of Pseudomonas fluorescens CHA0 is required for suppression of root diseases in dicotyledons but not in Gramineae. Plant Pathol 46:80-90 (Pubitemid 27121420)
50. Serino L, Reimmann C, Baur H, Beyeler M, Visca P, Haas D (1995) Structural genes for salicylate biosynthesis from chorismate in Pseudomonas aeruginosa. Mol Gen Genet 249:217-228
51. Serino L, Reimmann C, Visca P, Beyeler M, Della Chiesa V, Haas D (1997) Biosynthesis of pyochelin and dihydroaeruginoic acid requires the iron-regulated pchDCBA operon in Pseudomonas aeruginosa. J Bacteriol 179:248-257 (Pubitemid 26428488)
52. Stover CK, Pham XQ, Erwin AL, Mizoguchi SD, Warrener P et al (2000) Complete genome sequence of Pseudomonas aeruginosa PAO1, an opportunistic pathogen. Nature 406: 959-964
53. Terano H, Nomoto K, Takase S (2002) Siderophore production and induction of iron-regulated proteins by a microorganism from rhizosphere of barley. Biosci Biotechnol Biochem 66:2471-2473 (Pubitemid 39251188)
54. Thieken A, Winkelmann G (1992) Rhizoferrin: a complexone type siderophore of the Mucorales and Entomophthorales (Zygomycetes). FEMS Microbiol Lett 94:37-42
55. Thomas MS (2007) Iron acquisition mechanisms of the Burkholderia cepacia complex. Biometals 20:431-452 (Pubitemid 46776579)
56. Tseng C-F, Burger A, Mislin GLA, Schalk IJ, Yu SS-F, Cahn SI, Abdallah MA (2006) Bacterial siderophores: the solution stoichiometry and coordination of the Fe(III) complexes of pyochelin and related compounds. J Biol Inorg Chem 11:419-432 (Pubitemid 44012025)
57. Visca P, Colotti G, Serino L, Verzili D, Orsi N, Chiancone E (1992) Metal regulation of siderophore synthesis in Pseudomonas aeruginosa and functional effects of siderophore-metal complexes. Appl Environ Microbiol 58: 2886-2893
58. Wandersman C, Delepelaire P (2004) Bacterial iron sources: from siderophores to hemophores. Annu Rev Microbiol 58:611-647 (Pubitemid 39551999)
59. Youard ZA, Reimmann C (2010) Stereospecific recognition of pyochelin and enantio-pyochelin by the PchR proteins in fluorescent pseudomonads. Microbiology 156:1772-1782
60. Youard ZA, Mislin GLA, Majcherczyk PA, Schalk IJ, Reimmann C (2007) Pseudomonas fluorescens CHA0 produces enantio-pyochelin, the optical antipode of the Pseudomonas aeruginosa siderophore pyochelin. J Biol Chem 282:35546-35553 (Pubitemid 350277122)
61. Zaitseva J, Lu J, Olechoski KL, Lamb AL (2006) Two crystal structures of the isochorismate pyruvate-lyase from Pseudomonas aeruginosa. J Biol Chem 281:33441-33449 (Pubitemid 46036725)