Cofactor-independent oxidases and oxygenases

Applied Microbiology and Biotechnology

Volumn 86, Issue 3, 2010, Pages 791-804

  Fetzner, Susanne ^a   Steiner, Roberto A ^b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

hydrolase fold; Cofactor independent enzymes; Oxidase; Oxygen; Oxygenase

Indexed keywords

COFACTOR-INDEPENDENT ENZYMES; COFACTORS; HYDROLASES; OXIDASE; OXYGENASES;

ALDEHYDES; BACTERIOLOGY; BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; BIOSYNTHESIS; CATALYSIS; CATALYSTS; GENETIC ENGINEERING; METAL IONS; OXYGEN; OXYGENATION; TRANSITION METAL COMPOUNDS; TRANSITION METALS;

ENZYMES;

3,5 DIHYDROXYPHENYLACETYL COA 1,2 DIOXYGENASE; COPROPORPHYRINOGEN OXIDASE; DIOXYGENASE; OXIDOREDUCTASE; OXYGENASE; PYRROLOQUINOLINEQUINONE; QUINOLONE DERIVATIVE; QUINONE DERIVATIVE; RENILLA LUCIFERIN 2 MONOOXYGENASE; TEICOPLANIN; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; URATE OXIDASE; VANCOMYCIN;

ALDEHYDE; ANTIBIOTICS; BIOTECHNOLOGY; CATALYSIS; ENZYME ACTIVITY; MARINE ENVIRONMENT; METABOLISM; MICROBIAL ACTIVITY; OXIDATION; OXYGEN; POLYP; PROTEIN;

BIOENGINEERING; BIOTECHNOLOGY; CATALYSIS; ENZYME SYNTHESIS; NONHUMAN; SHORT SURVEY;

COENZYMES; METABOLIC NETWORKS AND PATHWAYS; MODELS, CHEMICAL; MODELS, MOLECULAR; OXIDOREDUCTASES; OXYGEN;

BACTERIA (MICROORGANISMS); RENILLA; RENILLA LUCIFERASE;

EID: 77950626884     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-010-2455-0     Document Type: Short Survey

References (101)

1. Abell LM, Schloss JV (1991) Oxygenase side reactions of acetolactate synthase and other carbanion-forming enzymes. Biochemistry 30:7883-7887
2. Adams MA, Jia J (2005) Structural and biochemical evidence for an enzymatic quinone redox cycle in Escherichia coli. Identification of a novel quinol monooxygenase. J Biol Chem 280:8358-8363
3. Anderson JM, Cormier MJ (1973) Lumisomes, the cellular site of bioluminescence in coelenterates. J Biol Chem 248:2937-2943
4. Andrés J, Safont VS, Tapia O (1992) Straining the double bond in 1, 2-dihydroxyethylene. A simple theoretical model for the enediol moiety in Rubiscós substrate and analogs. Chem Phys Lett 198:515-520
5. Bauer I, Max N, Fetzner S, Lingens F (1996) 2, 4-Dioxygenases catalyzing N-heterocyclic-ring cleavage and formation of carbon monoxide. Purification and some properties of 1H-3-hydroxy-4- oxoquinaldine 2, 4-dioxygenase from Arthrobacter sp. Rü61a and comparison with 1H-3-hydroxy-4-oxoquinoline 2, 4-dioxygenase from Pseudomonas putida 33/1. Eur J Biochem 240:576-583 (Pubitemid 26321158)
6. Bauerly KA, Storms DH, Harris CB, Hajizadeh S, Sun MY, Cheung CP, Satre MA, Fascetti AJ, Tchaparian E, Rucker RB (2006) Pyrroloquinoline quinone nutritional status alters lysine metabolism and modulates mitochondrial DNA content in the mouse and rat. Biochim Biophys Acta 1760:1741-1748 (Pubitemid 44667261)
7. Beermann B, Guddorf J, Boehm K, Albers A, Kolkenbrock S, Fetzner S, Hinz HJ (2007) Stability, unfolding, and structural changes of cofactor-free 1H-3-hydroxy-4-oxoquinaldine 2, 4-dioxygenase. Biochemistry 46:4241-4249 (Pubitemid 46559391)
8. Boehm K, Guddorf J, Albers A, Kamiyama T, Fetzner S, Hinz HJ (2008) Thermodynamic analysis of denaturant-induced unfolding of HodC69S protein supports a three-state mechanism. Biochemistry 47:7116-7126 (Pubitemid 351956360)
9. Bruice TC (1984) Oxygen-flavin chemistry. Isr J Chem 24:54-61
10. Bugg TDH (2003) Dioxygenase enzymes: catalytic mechanisms and chemical models. Tetrahedron 59:7075-7101
11. Busi E, Terzuoli L, Basosi R, Porcelli B, Marinello E (2004) EPR spin trapping of a radical intermediate in the urate oxidase reaction. Nucleosides Nucleotides Nucleic Acids 23:1131-1134 (Pubitemid 39625882)
12. Carlson BL, Ballister ER, Skordalakes E, King DS, Breidenbach MA, Gilmore SA, Berger JM, Bertozzi CR (2008) Function and structure of a prokaryotic formylglycine-generating enzyme. J Biol Chem 283:20117-20125
13. Carrico IS, Carlson BL, Bertozzi CR (2007) Introducing genetically encoded aldehydes into proteins. Nat Chem Biol 3:321-322
14. Chen H, Tseng CC, Hubbard BK, Walsh CT (2001) Glycopeptide antibiotic biosynthesis: enzymatic assembly of the dedicated amino acid monomer (S)-3, 5-dihydroxyphenylglycine. Proc Natl Acad Sci USA 98:14901-14906 (Pubitemid 34013942)
15. Chun CK, Ozer EA, Welsh MJ, Zabner J, Greenberg EP (2004) Inactivation of a Pseudomonas aeruginosa quorum-sensing signal by human airway epithelia. Proc Natl Acad Sci USA 101:3587-3590 (Pubitemid 38338239)
16. Chung JY, Fujii I, Harada S, Sankawa U, Ebizuka Y (2002) Expression, purification, and characterization of AknX anthrone oxygenase, which is involved in aklavinone biosynthesis in Streptomyces galilaeus. J Bacteriol 184:6115-6122 (Pubitemid 35265891)
17. Colloc'h N, El Hajji M, Bachet B, ĹHermite G, Schiltz M, Prangé T, Castro B, Mornon JP (1997) Crystal structure of the protein drug urate oxidase-inhibitor complex at 2.05 Å resolution. Nat Struct Biol 4:947-952 (Pubitemid 27479447)
18. Colloc'h N, Gabison L, Monard G, Altarsha M, Chiadmi M, Marassio G, Santos JSDO, El Hajji M, Castro B, Abraini JH, Prangé T (2008) Oxygen pressurized X-ray crystallography: probing the dioxygen binding site in cofactorless urate oxidase and implications for its catalytic mechanism. Biophys J 95:2415-2422
19. Cormier MJ, Lee J, Wampler JE (1975) Bioluminescence: recent advances. Annu Rev Biochem 44:255-272
20. Das A, Khosla C (2009) Biosynthesis of aromatic polyketides in bacteria. Acc Chem Res 42:631-639
21. Dierks T, Dickmanns A, Preusser-Kunze A, Schmidt B, Mariappan M, von Figura K, Ficner R, Rudolph MG (2005) Molecular basis for multiple sulfatase deficiency and mechanism for formylglycine generation of the human formylglycine-generating enzyme. Cell 121:541-552 (Pubitemid 40720008)
22. Dierks T, Schlotawa L, Frese MA, Radhakrishnan K, von Figura K, Schmidt B (2009) Molecular basis of multiple sulfatase deficiency, mucolipidosis II/III and Niemann-Pick C1 disease-lysosomal storage disorders caused by defects of non-lysosomal proteins. Biochim Biophys Acta 1793:710-725
23. Dierks T, Schmidt B, Borissenko LV, Peng JK, Preusser A, Mariappan M, von Figura K (2003) Multiple sulfatase deficiency is caused by mutations in the gene encoding the human Cα-formylglycine generating enzyme. Cell 113:435-444 (Pubitemid 36588747)
24. Diggle SP, Cornelis P, Williams P, Camara M (2006) 4-Quinolone signalling in Pseudomonas aeruginosa: old molecules, new perspectives. Int J Med Microbiol 296:83-91 (Pubitemid 43375990)
25. Doll C, Bell AF, Power N, Tonge PJ, Tipton PA (2005) Procatalytic ligand strain. Ionization and perturbation of 8-nitroxanthine at the urate oxidase active site. Biochemistry 44:11440-11446 (Pubitemid 41209079)
26. Dubern JF, Diggle SP (2008) Quorum sensing by 2-alkyl-4-quinolones in Pseudomonas aeruginosa and other bacterial species. Mol Biosyst 4:882-888
27. Fetzner S (2002) Oxygenases without requirement for cofactors or metal ions. Appl Microbiol Biotechnol 60:243-257 (Pubitemid 35352091)
28. Fetzner S (2007) Cofactor-independent oxygenases go it alone. Nat Chem Biol 3:374-375 (Pubitemid 46956336)
29. Fielding EN, Widboom PF, Bruner SD (2007) Substrate recognition and catalysis by the cofactor-independent dioxygenase DpgC. Biochemistry 46:13994-14000 (Pubitemid 350250296)
30. Fischer F, Fetzner S (2000) Site-directed mutagenesis of potential catalytic residues in 1H-3-hydroxy-4-oxoquinoline 2, 4-dioxygenase, and hypothesis on the catalytic mechanism of 2, 4-dioxygenolytic ring cleavage. FEMS Microbiol Lett 190:21-27 (Pubitemid 30645829)
31. Fischer F, Künne S, Fetzner S (1999) Bacterial 2, 4-dioxygenases: new members of the α/β hydrolase-fold superfamily of enzymes functionally related to serine hydrolases. J Bacteriol 181:5725-5733 (Pubitemid 29437144)
32. Fleming SM, Robertson TA, Langley GJ, Bugg TDH (2000) Catalytic mechanism of a C-C hydrolase enzyme: evidence for a gem-diol intermediate, not an acyl enzyme. Biochemistry 39:1522-1531
33. Frerichs-Deeken U, Ranguelova K, Kappl R, Hüttermann J, Fetzner S (2004) Dioxygenases without requirement for cofactors and their chemical model reaction: compulsory order ternary complex mechanism of 1H-3-hydroxy-4- oxoquinaldine 2, 4-dioxygenase involving general base catalysis by histidine 251 and singleelectron oxidation of the substrate dianion. Biochemistry 43:14485-14499 (Pubitemid 39491983)
34. Frese MA, Dierks T (2009) Formylglycine aldehyde tag-protein engineering through a novel post-translational modification. ChemBioChem 10:425-427
35. Gabison L, Prangé T, Colloc'h N, El Hajji M, Castro B, Chiadmi M (2008) Structural analysis of urate oxidase in complex with its natural substrate inhibited by cyanide: mechanistic implications. BMC Struct Biol 8:32
36. Goto T (1968) Chemistry of bioluminescence. Pure Appl Chem 17:421-441
37. Hanson SR, Best MD, Wong CH (2004) Sulfatases: structure, mechanism, biological activity, inhibition, and synthetic utility. Angew Chem Int Ed 43:5736-5763
38. Hart RC, Stempel KE, Boyer PD, Cormier MJ (1978) Mechanism of the enzyme-catalyzed bioluminescent oxidation of coelenteratetype luciferin. Biochem Biophys Res Commun 81:980-986
39. Hastings JW (2004) Bacterial quorum-sensing signals are inactivated by mammalian cells. Proc Natl Acad Sci USA 101:3993-3994
40. Hori K, Wampler JE, Matthews JC, Cormier MJ (1973) Bioluminescence of Renilla reniformis. XIII. Identification of the product excited states during the chemiluminescent and bioluminescent oxidation of Renilla (sea pansy) luciferin and certain of its analogs. Biochemistry 12:4463-4468
41. Imhoff RD, Power NP, Borrok MJ, Tipton PA (2003) General base catalysis in the urate oxidase reaction: evidence for a novel Thr- Lys catalytic diad. Biochemistry 42:4094-4100
42. Johnson RJ, Kang DH, Feig D, Kivlighn S, Kanellis J, Watanabe S, Tuttle KR, Rodriguez-Iturbe B, Herrera-Acosta J, Mazzali M (2003) Is there a pathogenic role for uric acid in hypertension and cardiovascular and renal disease? Hypertension 41:1183-1190 (Pubitemid 36706063)
43. Juan ECM, Hoque MM, Shimizu S, Hossain MT, Yamamoto T, Imamura S, Suzuki K, Tsunoda M, Amano H, Sekiguchi T, Takénaka A (2008) Structures of Arthrobacter globiformis urate oxidase-ligand complexes. Acta Cryst D64:815-822
44. Kahn K, Serfozo P, Tipton PA (1997) Identification of the true product of the urate oxidase reaction. J Am Chem Soc 119:5435-5442 (Pubitemid 27310720)
45. Kahn K, Tipton PA (1997) Kinetic mechanism and cofactor content of soybean root nodule urate oxidase. Biochemistry 36:4731-4738 (Pubitemid 27180953)
46. Kahn K, Tipton PA (1998) Spectroscopic characterization of intermediates in the urate oxidase reaction. Biochemistry 37:11651-11659 (Pubitemid 28388209)
47. Kendrew SG, Hopwood DA, Marsh ENG (1997) Identification of a monooxygenase from Streptomyces coelicolorA3(2) involved in biosynthesis of actinorhodin: purification and characterization of the recombinant enzyme. J Bacteriol 179:4305-4310
48. Kertesz MA (2000) Riding the sulfur cycle-metabolism of sulfonates and sulfate esters in Gram-negative bacteria. FEMS Microbiol Rev 24:135-175
49. Killgore J, Smidt C, Duich L, Romero-Chapman N, Tinker D, Reiser K, Melko M, Hyde D, Rucker RB (1989) Nutritional importance of pyrroloquinoline quinone. Science 245:850-852 (Pubitemid 19223660)
50. Kutzing MK, Firestein BL (2008) Altered uric acid levels and disease states. J Pharmacol Exp Ther 324:1-7
51. Lash TD (2005) The enigma of coproporphyrinogen oxidase: how does this unusual enzyme carry out oxidative decarboxylations to afford vinyl groups? Biooorg Med Chem Lett 15:4506-4509
52. Lee DS, Flachsová E, Bodnárová M, Demeler B, Martásek P, Raman CS (2005) Structural basis of hereditary coproporphyria. Proc Natl Acad Sci USA 102:14232-14237 (Pubitemid 41429681)
53. Leisinger T, Margraff R (1979) Secondary metabolites of the fluorescent pseudomonads. Microbiol Rev 43:422-442 (Pubitemid 10200223)
54. Li JJ, Bugg TDH (2007) Investigation of a general base mechanism for ester hydrolysis in C-C hydrolase enzymes of the α/β- hydrolase superfamily: a novel mechanism for the serine catalytic triad. Org Biomol Chem 5:507-513
55. Loening AM, Fenn TD, Gambhir SS (2007) Crystal structures of the luciferase and green fluorescent protein from Renilla reniformis. J Mol Biol 374:1017-1028 (Pubitemid 350064511)
56. Loening AM, Fenn TD, Wu AM, Gambhir SS (2006) Consensus guided mutagenesis of Renilla luciferase yields enhanced stability and light output. Prot Eng Des Sel 19:391-400
57. Lombó F, Abdelfattah MS, Braña AF, Salas JA, Rohr H, Méndez C (2009) Elucidation of oxygenation steps during oviedomycin biosynthesis and generation of derivatives with increased antitumor activity. ChemBioChem 10:296-303
58. Magnusson OT, RoseFigura JM, Toyama H, Schwarzenbacher R, Klinman JP (2007) Pyrroloquinoline quinone biogenesis: characterization of PqqC and its H84N and H84A active site variants. Biochemistry 46:7174-7186 (Pubitemid 46973991)
59. Magnusson OT, Toyama H, SaekiM, Rojas A, Reed JC, Liddington RC, Klinman JP, Schwarzenbacher R (2004) Quinone biogenesis: structure and mechanism of PqqC, the final catalyst in the production of pyrroloquinoline quinone. Proc Natl Acad Sci USA 101:7913-7918 (Pubitemid 38698028)
60. Massey V (1994) Activation of molecular oxygen by flavins and flavoproteins. J Biol Chem 269:22459-22462 (Pubitemid 24273342)
61. Matthews JC, Hori K, Cormier MJ (1977) Substrate and substrate analogue binding properties of Renilla luciferase. Biochemistry 16:5217-5220 (Pubitemid 8241838)
62. Max N, Betz A, Facey S, Lingens F, Hauer B, Fetzner S (1999) Cloning, sequence analysis, and expression of the Pseudomonas putida 33/1 1H-3-hydroxy-4-oxoquinoline 2, 4-dioxygenase gene, encoding a carbon monoxide forming dioxygenase. Biochim Biophys Acta 1431:547-552
63. Oliva M, Safont VS, Andrés J, Tapia O (2001) Transition structures for D-ribulose-1, 5-bisphosphate carboxylase/oxygenase-catalyzed oxygenation chemistry: role of carbamylated lysine in a model magnesium coordination sphere. J Phys Chem A 105:4726-4736
64. Ouchi A, Nakano M, Nagaoka SI, Mukai K (2009) Kinetic study of the antioxidant activity of pyrroloquinolinequinol (PQQH2, a reduced form of pyrroloquinolinequinone) in micellar solution. J Agric Food Chem 57:450-456
65. Palfey BA, Ballou DP, Massey V (1995) Oxygen activation by flavins and pterins. In: Selverstone Valentine J, Foote CS, Greenberg A, Liebman JF (eds) Active oxygen in biochemistry. Blackie Academic and Professional (Chapman and Hall), London, pp 37-83
66. Parschat K, Overhage J, Strittmatter AW, Henne A, Gottschalk G, Fetzner S (2007) Complete nucleotide sequence of the 113-kilobase linear catabolic plasmid pAL1 of Arthrobacter nitroguajacolicus Rü61a and transcriptional analysis of genes involved in quinaldine degradation. J Bacteriol 189:3855-3867 (Pubitemid 46740183)
67. Pesci EC, Milbank JBJ, Pearson JP, McKnight S, Kende AS, Greenberg EP, Iglewski BH (1999) Quinolone signaling in the cell-to-cell communication system of Pseudomonas aeruginosa. Proc Natl Acad Sci USA 96:11229-11234
68. Phillips JD, Whitby FG, Warby CA, Labbe P, Yang C, Pflugrath JW, Ferrara JD, Robinson H, Kushner JP, Hill CP (2004) Crystal structure of the oxygen-dependent coproporphyrinogen oxidase (Hem13p) of Saccharomyces cerevisiae. J Biol Chem 279:28960-38968 (Pubitemid 39296057)
69. Preusser-Kunze A, Mariappan M, Schmidt B, Gande SL, Mutenda K, Wenzel D, von Figura K, Dierks T (2005) Molecular characterization of the human Cα-formylglycine-generating enzyme. J Biol Chem 280:14900-14910 (Pubitemid 40562840)
70. Prokop Z, Monincová M, Chaloupková R, Klvana M, Nagata Y, Janssen DB, Damborský J (2003) Catalytic mechanism of the haloalkane dehalogenase LinB from Sphingomonas paucimobilis UT26. J Biol Chem 278:45094-45100 (Pubitemid 37432641)
71. Pustelny C, Albers A, Büldt-Karentzopoulos K, Parschat K, Chhabra SR, Camara M, Williams P, Fetzner S (2009) Dioxygenasemediated quenching of quinolone-dependent quorum sensing in Pseudomonas aeruginosa. Chem Biol 16:1259-1267
72. Rafanan ER Jr, Le L, Zhao L, Decker H, Shen B (2001) Cloning, sequencing, and heterologous expression of the elmGHIJ genes involved in the biosynthesis of the polyketide antibiotic Elloramycin from Streptomyces olivaceus Tü2353. J Nat Prod 64:444-449 (Pubitemid 32423868)
73. Rasmussen TB, Givskov M (2006) Quorum sensing inhibitors: a bargain of effects. Microbiology 152:895-904
74. Rees JF, de Wergifosse B, Noiset O, Dubuisson M, Janssens B, Thompson EM (1998) The origins of marine bioluminescence: turning oxygen defence mechanisms into deep-sea communication tools. J Exp Biol 201:1211-1221 (Pubitemid 28278325)
75. Roeser D, Preusser-Kunze A, Schmidt B, Gasow K, Wittmann JG, Dierks T, von Figura K, Rudolph MG (2006) A general binding mechanism for all human sulfatases by the formylglycinegenerating enzyme. Proc Natl Acad Sci USA 103:81-86 (Pubitemid 43076108)
76. Roeser D, Schmidt B, Preusser-Kunze A, Rudolph MG (2007) Probing the oxygen-binding site of the human formylglycinegenerating enzyme using halide ions. Acta Cryst D63:621-627
77. Rothfork JM, Timmins GS, Harris MN, Chen X, Lusis AJ, Otto M, Cheung AL, Gresham HD (2004) Inactivation of a bacterial virulence pheromone by phagocyte-derived oxidants: new role for the NADPH oxidase in host defense. Proc Natl Acad Sci USA 101:13867-13872
78. Rush JS, Bertozzi CR (2008) New aldehyde tag sequences identified by screening formylglycine generating enzymes in vitro and in vivo. J Am Chem Soc 130:12240-12241
79. Sarma AD, Tipton PA (2000) Evidence for urate hydroperoxide as an intermediate in the urate oxidase reaction. J Am Chem Soc 122:11252-11253
80. Sassa S (2006) Modern diagnosis and management of the porphyrias. Br J Haematol 135:281-292
81. Schwarzenbacher R, Stenner-Liewen F, Liewen H, Reed JC, Liddington RC (2004) Crystal structure of PqqC from Klebsiella pneumoniae at 2.1 Å resolution. Proteins 56:401-403
82. Sciara G, Kendrew SG, Miele AE, Marsh NG, Federici L, Malatesta F, Schimperna G, Savino C, Vallone B (2003) The structure of ActVA-Orf6, a novel type of monooxygenase involved in actinorhodin biosynthesis. EMBO J 22:205-215
83. Shen B, Hutchinson CR (1993) Tetracenomycin F1 monooxygenase: oxidation of a naphthacenone to a naphthacenequinone in the biosynthesis of tetracenomycin C in Streptomyces glaucescens. Biochemistry 32:6656-6663 (Pubitemid 23217135)
84. Sherman MR, Saifer MGP, Perez-Ruiz F (2008) PEG-uricase in the management of treatment-resistant gout and hyperuricemia. Adv Drug Deliv Rev 60:59-68
85. Silva PJ, Ramos MJ (2008) A comparative density-functional study of the reaction mechanism of the O2-dependent coproporphyrinogen III oxidase. Biooorg Med Chem 16:2726-2733
86. Smith RS, Iglewski BH (2003) Pseudomonas aeruginosa quorum sensing as a potential antimicrobial target. J Clin Invest 112:1460-1465
87. Spurlock BO, Cormier MJ (1975) A fine structure study of the anthocodium in Renilla mülleri. Evidence for the existence of a bioluminescent organelle, the luminelle. J Cell Biol 64:15-28
88. Stec B, Stieglitz KA (2008) Not so clear on oxygen. Comment on Structural basis for cofactor-independent dioxygenation in vancomycin biosynthesis by Widboom et al. (2007), Nature (London), 447, 342-345. Acta Cryst D64:1000-1002
89. Steiner RA, Janßen HJ, Roversi P, Oakley AJ, Fetzner S (2010) Structural basis for cofactor-independent dioxygenation of Nheteroaromatic compounds at the α/β hydrolase fold. Proc Natl Acad Sci USA 107:657-662
90. Stepanyuk GA, Liu ZJ, Vysotski ES, Lee J, Rose JP, Wang BC (2009) Structure based mechanism of the Ca2+-induced release of coelenterazine from the Renilla binding protein. Proteins 74:583-593
91. Stephenson JR, Stacey JA, Morgenthaler JB, Friesen JA, Lash TD, Jones MA (2007) Role of aspartate 400, arginine 262, and arginine 401 in the catalytic mechanism of human coproporphyrinogen oxidase. Protein Sci 16:401-410
92. Tipton PA (2002) Urate oxidase: single-turnover stopped-flow techniques for detecting two discrete enzyme-bound intermediates. Methods Enzymol 354:310-319
93. Tseng CC, Vaillancourt FH, Bruner SD, Walsh CT (2004) DpgC is a metal- and cofactor-free 3, 5-dihydroxyphenylacetyl-CoA 1, 2-dioxygenase in the vancomycin biosynthetic pathway. Chem Biol 11:1195-1203
94. Walsh CT (2008) The chemical versatility of natural-product assembly lines. Acc Chem Res 41:4-10
95. Wang Y, Scherperel G, Roberts KD, Jones AD, Reid GE, Yan H (2006) A point mutation converts dihydroneopterin aldolase to a cofactorindependent oxygenase. J Am Chem Soc 128:13216-13223
96. Ward WW, Cormier MJ (1979) An energy transfer protein in coelenterate bioluminescence. Characterization of the Renilla green-fluorescent protein. J Biol Chem 254:781-788
97. Widboom PF, Fielding EN, Liu Y, Bruner SD (2007) Structural basis for cofactor-independent dioxygenation in vancomycin biosynthesis. Nature 447:342-345
98. Wilson T, Hastings JW (1998) Bioluminescence. Annu Rev Cell Dev Biol 14:197-230
99. Woo J, Howell MH, von Arnim AG (2008) Structure-function studies on the active site of the coelenterazine-dependent luciferase from Renilla. Protein Sci 17:725-735 (Pubitemid 351480866)
100. Wu P, Shui WQ, CarlsonBL HuN, Rabuka D, Lee J, Bertozzi CR (2009) Site-specific chemical modification of recombinant proteins produced in mammalian cells by using the genetically encoded aldehyde tag. Proc Natl Acad Sci USA 106:3000-3005
101. Yang F, Wang LH, Wang J, Dong YH, Hu JY, Zhang LH (2005) Quorum quenching enzyme activity is widely conserved in the sera of mammalian species. FEBS Lett 579:3713-3717 (Pubitemid 40897714)