Diverse reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp strain NCIB 9816

Journal of Industrial Microbiology and Biotechnology

Volumn 17, Issue 5-6, 1996, Pages 438-457

  Resnick, S M ^a   Lee, K ^a   Gibson, D T ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

Asymmetric dihydroxylation; Biocatalysis; Biotransformation; Dealkylation; Desaturation; Dioxygenation; Monooxygenation; Stereospecific oxidation; Sulfoxidation

Indexed keywords

NAPHTHALENE DIOXYGENASE; OXIDOREDUCTASE; UNCLASSIFIED DRUG;

ENANTIOMER; ENZYME ACTIVITY; ENZYME SPECIFICITY; PSEUDOMONAS; REVIEW;

EID: 0030513196     PISSN: 13675435     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (104)

1. Agarwal R, DR Boyd, RAS McMordie, GA O'Kane, P Porter ND Sharma, H Dalton and DJ Gray. 1990. Chiral arene hydrates of naphthalene: enzymatic and chemical syntheses. J Chem Soc Chem Comm 1711-1713.
2. Akhtar MN, DR Boyd, NJ Thompson, M Koreeda, DT Gibson, V Mahadevan and DM Jerina. 1975. Absolute stereochemistry of the dihydroanthracene-cis- and -trans-1,2-diols produced from anthracene by mammals and bacteria. J Chem Soc Perkin I 2506-2511.
3. Allen CCR, DR Boyd, H Dalton, ND Sharma, I Brannigan, NA Kerley, GN Sheldrake and SC Taylor. 1995. Enantioselective bacterial biotransformation routes to cis-diol metabolites of monosubstituted benzenes, naphthalene and benzocydoalkenes of either absolute configuration. J Chem Soc Chem Commun 117-118.
4. Allen CCR, DR Boyd, H Dalton, ND Sharma, SA Haughey, RAS McMordie, BT McMurray, GN Sheldrake and K Sproule. 1995. Sulfoxides of high enantiopurity from bacterial dioxygenase-catalyzed oxidation. J Chem Soc Chem Commun 119-120.
5. Ballou D and C Batie. 1988. Phthalate oxygenase, a Rieske iron-sulfur protein from Pseudomonas cepacia. In: Proceedings of the Fourth International Symposium on Oxidases and Related Redox Systems (King TE, HS Mason and M Morrison, eds), pp 211-226, Alan R Liss, New York.
6. Barr SA, DR Boyd, ND Sharma, L Hamilton, RAS McMordie and H Dalton. 1994. Bacterial aromatic hydroxylation: cis-dihydrodiol metabolites and their possible role in the 'NIH Shift'. J Chem Soc Chem Commun 1921.
7. Batie CJ, DP Ballou and CC Corell. 1991. Phthalate dioxygenase reductase and related flavin-iron-sulfur containing electron transferases. In: Chemistry and Biochemistry of Flavoenzymes (Müller F, ed), pp 543-556, CRC Press, Boca Raton, FL.
8. Bernhardt F-H, E Bill, AX Trautwein and H Twilfer. 1988. 4-Methoxybenzoate monooxygenase from Pseudomonas putida: isolation, biochemical properties, substrate specificity, and reaction mechanisms of the enzyme components. Meth Enzymol 161: 281-294.
9. Bestetti G, D Bianchi, A Bosetti, P Di Gennaro, E Galli, B Leoni, F Pelizzoni and G Sello. 1995. Bioconversion of substituted naphtha-lenes to the corresponding 1,2-dihydro-1,2-dihydroxy derivatives. Determination of the regio- and stereochemistry of the oxidation reactions. Appl Microbiol Biotechnol 44: 306-313.
10. Blumer M. 1975. Organic compounds in nature: limits of our knowledge. Angew Chem Int Edit 14: 507-580.
11. Boyd DR, MRJ Dorrity, MV Hand, JF Malone and ND Sharma. 1991. Enantiomeric excess and absolute configuration determination of cis-dihydrodiols from bacterial metabolism of monocylic arenes. J Am Chem Soc 113: 666-667.
12. Boyd DR, MRJ Dorrity, JF Malone, RAS McMordie, ND Sharma, H Dalton and P Williams. 1990. Bacterial metabolism of 6,7-dihydro-5H-benzocycloheptene by Pseudomonas putida. Synthesis and absolute configuration of benzylic alcohol and cis-diol metabolites of 6,7-dihydro-5H-benzocycloheptene. J Chem Soc Perkin Trans 1 489-494.
13. Boyd DR, RAS McMordie, ND Sharma, H Dalton, P Williams and RO Jenkins. 1989. Stereospecific benzylic hydroxylation of bicyclic alkenes by Pseudomonas putida: isolation of (+)-R-1-hydroxy-1,2-dihydronaphthalene, an arene hydrate of naphthalene from metabolism of 1,2-dihydronaphthalene. J Chem Soc Chem Commun 339-340.
14. Boyd DR, ND Sharma, R Boyle, JF Malone, J Chima and H Dalton. 1993. Structures and stereochemical assignments of some novel chiral synthons derived from the biotransformation of 2,3-dihydrobenzofuran and benzofuran by Pseudomonas putida. Tetrahedron: Asymmetry 4: 1307-1324.
15. 1H-NMR method for the determination of enantiomeric excess and absolute configuration of cis-dihydrodiol metabolites of polycyclic arenes and heteroarenes. Tetrahedron Lett 33: 1241-1244.
16. Boyd DR, ND Sharma and H Dalton. 1995. Enzyme-catalyzed hydroxylation of aromatic substrates: stereochemical and mechanistic aspects. In: Organic Reactivity: Physical and Biological Aspects (Golding BT, RJ Griffin and H Maskill, eds), pp 130-139, The Royal Society of Chemistry, Cambridge, UK.
17. Boyd DR, ND Sharma, NA Kerley, RAS McMordie, GN Sheldrake, P Williams and H Dalton. 1996. Dioxygenase-catalyzed oxidation of dihydronaphthalenes to yield arene hydrate and cis-dihydro naphthalenediols. J Chem Soc, Perkin Trans 1 67-74.
18. Boyd DR, ND Sharma, PJ Stevenson, J Chima, DJ Gray and H Dalton. 1991. Bacterial oxidation of benzocycloalkenes to yield monol, diol and triol metabolites. Tetrahedron Lett 32: 3887-3890.
19. Brilon C, W Beckmann and H-J Knackmuss. 1981. Catabolism of naphthalenesulfonic acids by Pseudomonas sp A3 and Pseudomonas sp C22. Appl Environ Microbiol 42: 44-55.
20. Brown SM and T Hudlicky. 1993. The use of arene-cis-diols in synthesis. In: Organic Synthesis: Theory and Applications (Hudlicky T, ed), pp 113-176, JAI Press, Greenwich, CT.
21. Carless HAJ. 1992. The use of cyclohexa-3,5-diene-1,2-diols in enantiospecific synthesis. Tetrahedron: Asymmetry 3: 795-826.
22. Cashman JR, LD Olsen, DR Boyd, RAS McMordie, R Dunlop and H Dalton. 1992. Stereoselectivity of enzymatic and chemical oxygenation of sulfur atoms in 2-methyl-1,3-benzodithiole. J Am Chem Soc 114: 8772-8777.
23. Catterall FA, K Murray and PA Williams. 1971. The configuration of the 1,2-dihydroxy-1,2-dihydronaphthalene formed in the bacterial metabolism of naphthalene. Biochim Biophys Acta 237: 361-364.
24. Catterall FA and PA Williams. 1971. Some properties of the naphthalene oxygenase from Pseudomonas sp NCIB 9816. J Gen Microbiol 67: 117-124.
25. Cerniglia CE. 1992. Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation 3: 351-368.
26. Chapman PJ. 1972. An outline of reaction sequences used for the bacterial degradation of phenolic compounds. In: Degradation of Synthetic Organic Molecules in the Biosphere: Natural, Pesticidal, and Various Other Man-made Compounds, pp 17-45, National Academy of Sciences, Washington DC.
27. Davies JI and WC Evans. 1964. Oxidative metabolism of naphthalene by soil pseudomonads: the ring-fission mechanism. Biochem J 91: 251-261.
28. Deluca ME and T Hudlicky. 1990. Microbial oxidation of naphthalene derivatives. Absolute configuration of metabolites. Tetrahedron Lett 31: 13-16.
29. Eaton RW and PJ Chapman. 1992. Bacterial metabolism of naphthalene: construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxynaphthalene and subsequent reactions. J Bacteriol 174: 7542-7554.
30. Ensley BD and DT Gibson. 1983. Naphthalene dioxygenase: purification and properties of a terminal oxygenase component. J Bacteriol 155: 505-511.
31. Ensley BD, DT Gibson and AL Laborde. 1982. Oxidation of naphthalene by a multicomponent enzyme system from Pseudomonas sp strain NCIB 9816. J Bacteriol 149: 948-954.
32. Ensley BD, BJ Ratzkin, TD Osslund, MJ Simon, LP Wackett and DT Gibson. 1983. Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. Science 222: 167-169.
33. Evans WC, HN Fernley and E Griffiths. 1965. Oxidative metabolism of phenanthrene and anthracene by soil pseudomonads: the ring-fission mechanism. Biochem J 95: 819-831.
34. Feig AL and SJ Lippard. 1994. Reactions of non-heme iron(II) centers with dioxygen in biology and chemistry. Chem Rev 94: 759-805.
35. Gassner GT, DP Ballou, GA Landrum and JW Whittaker. 1993. Magnetic circular dichroism studies on the mononuclear ferrous active site of phthalate dioxygenase from Pseudomonas cepacia show a change of ligation state on substrate binding. Biochemistry 32: 4820-4825.
36. Gibson DT, GE Cardini, FC Masales and RE Kallio. 1970. Incorporation of oxygen-18 into benzene by Pseudomonas putida. Biochemistry 9: 1631-1635.
37. Gibson DT, M Hensley, H Yoshioka and TJ Mabry. 1970. Formation of (+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene from toluene by Pseudomonas putida. Biochemistry 9: 1626-1630.
38. Gibson DT, SM Resnick, K Lee, JM Brand, DS Torok, LP Wackett, MJ Schocken and BE Haigler. 1995. Desaturation, dioxygenation and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp strain 9816-4. J Bacteriol 177: 2615-2621.
39. Gibson DT and V Subramanian. 1984. Microbial degradation of aromatic hydrocarbons. In: Microbial Degradation of Organic Compounds (Gibson DT, ed), pp 181-251, Marcel Dekker, New York, NY.
40. Gibson DT, GJ Zylstra and S Chauhan. 1990. Biotransformations catalyzed by toluene dioxygenase from Pseudomonas putida F1. In: Pseudomonas: biotransformations, pathogenesis, and evolving biotechnology (Silver S, AM Chakrabarty, B Iglewski and S Kaplan, ed), pp 121-132, American Society for Microbiology, Washington DC.
41. Green J and H Dalton. 1989. Substrate specificity of soluble methane monooxygenase: mechanistic implications. J Biol Chem 264: 17698-17703.
42. Guengerich FP. 1990. Enzymatic oxidation of xenobiotic chemicals. Crit Rev Biochem Mol Biol 25: 97-153.
43. Guengerich FP. 1991. Reactions and significance of cytochrome P-450 enzymes. J Biol Chem 266: 10019-10022.
44. Haigler BE. 1986. PhD thesis. The University of Texas, Austin, TX.
45. NAP, a component of naphthalene dioxygenase from Pseudomonas sp strain NCIB 9816. J Bacteriol 172: 465-468.
46. NAP reductase, a component of naphthalene dioxygenase from Pseudomonas sp strain NCIB 9816. J Bacteriol 172: 457-464.
47. Hudlicky T, EE Boros and CH Boros. 1993. New diol metabolites derived by biooxidation of chorostyrenes with Pseudomonas putida: determination of absolute stereochemistry and enantiomeric excess by convergent syntheses. Tetrahedron: Asymmetry 4: 1365-1386.
48. Hudlicky T, H Luna, JD Price and F Rulin. 1990. Microbial oxidation of chloroaromatics in enantiodivergent synthesis of pyrrolizidine alkaloids: trihydroxyheliotridanes. J Org Chem 55: 4683-4687.
49. Hudlicky T and JW Reed. 1995. An evolutionary perspective of microbial oxidations of aromatic compounds in enantioselective synthesis: history, current status, and perspectives. In: Advances in Asymmetric Synthesis, pp 271-312, JAI Press, Greenwich, CT.
50. Hudlicky T, MR Stabile, DT Gibson and GM Whited. 1996. 1-Chloro-(2S,3S)-dihydroxycyclohexa-4,6-diene. Organic Synthesis (submitted).
51. Jeffrey AM, HJC Yen, DM Jerina, TR Patel, JF Davey and DT Gibson. 1975. Initial reactions in the oxidation of naphthalene by Pseudomonas putida. Biochemistry 14: 575-583.
52. Jerina DM and JW Daly. 1974. Arene oxides: a new aspect of drug metabolism. Science 185: 573-582.
53. Jerina DM, JW Daly, AM Jeffrey and DT Gibson. 1971. cis-1,2-Dihydroxy-1,2-dihydronaphthalene: a bacterial metabolite from naphthalene. Arch Biochem Biophys 142: 394-396.
54. Jerina DM, H Selander, H Yagi, MC Wells, JF Davey, V Mahadevan and DT Gibson. 1976. Dihydrodiols from anthracene and phenanthrene. J Am Chem Soc 98: 5988-5996.
55. Jiang H, RC Parales, NA Lynch and DT Gibson. 1996. Site-directed mutagenesis of conserved amino acids in the alpha subunit of toluene dioxygenase: potential mononuclear non-heme iron coordination sites. J Bacteriol 178: 3133-3139.
56. Khan AA, R-F Wang, W-W Cao, W Franklin and CE Cerniglia. 1996. Reclassification of a polycyclic aromatic hydrocarbon-metabolizing bacterial strain, Beijerinckia sp strain B1, as Sphingomonas yanoikuyae by fatty acid analysis, protein pattern analysis, and 16S rDNA sequencing. Int J Sys Bacteriol 46: 466-469.
57. Klecka GM and DT Gibson. 1979. Metabolism of dibenzo[1,4]dioxan by a Pseudomonas species. Biochem J 180: 639-645.
58. Knackmuss H-J, W Beckmann and W Otting. 1976. Microbiological synthesis of (+)-cis-1,2-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid. Angew Chem Int Ed Engl 15: 549.
59. Kobal VM, DT Gibson, RE Davis and A Garza. 1973. X-ray determination of the absolute stereochemistry of the initial oxidation product formed from toluene by Pseudomonas putida 39/D. J Am Chem Soc 95: 4420-4421.
60. Kolb HC, MS VanNieuwenhze and KB Sharpless. 1994. Catalytic asymmetric dihydroxylation. Chem Rev 94: 2483-2547.
61. Koreeda M, MN Akhtar, DR Boyd, JD Neill, DT Gibson and DM Jerina. 1978. Absolute stereochemistry of cis-1,2-, trans-1,2-, and cis-3,4-dihydrodiol metabolites of phenanthrene. J Org Chem 43: 1023-1027.
62. Kurkela S, H Lehvaslaiho, ET Palva and TH Teeri. 1988. Cloning, nucleotide sequence and characterization of genes encoding naphthalene dioxygenase of Pseudomonas putida strain NCIB 9816. Gene 73: 355-362.
63. Laborde AL and DT Gibson. 1977. Metabolism of dibenzothiophene by a Beijerinckia species. Appl Environ Microbiol 34: 783-790.
64. Lee K. 1995. PhD thesis. The University of Iowa, Iowa City, IA.
65. Lee K, JM Brand and DT Gibson. 1995. Stereospecific sulfoxidation by toluene and naphthalene dioxygenases. Biochem Biophys Res Commun 212: 9-15.
66. Lee K and DT Gibson. 1996. Stereospecific dihydroxylation of the styrene vinyl group by purified naphthalene dioxygenase from Pseudomonas sp strain 9816-4. J Bacteriol 178: 3353-3356.
67. Lee K and DT Gibson. 1996. Toluene and ethylbenzene oxidation by purified naphthalene dioxygenase from Pseudomonas sp strain NCIB 9816-4. Appl Environ Microbiol 62: 3101-3106.
68. Lee K, SM Resnick and DT Gibson. Stereospecific oxidation of (R)-and (S)-1-indanol by napthalene dioxygenase from Pseudomonas sp strain NCIB 9816-4. (submitted).
69. Lee K, SM Resnick and DT Gibson. 1995. Dioxygenase, monooxygenase, dehydrogenase and desaturase reactions catalyzed by purified naphthalene dioxygenase. O-58, p 378. Abstr 95th Gen Meet Amer Soc for Microbiol, Washington DC.
70. Ley SV. 1990. Stereoselective synthesis of inositol phosphates. Pure Appl Chem 62: 2031-2034.
71. Lipscomb JD. 1994. Biochemistry of the soluble methane monooxygenase. Annu Rev Microbiol 48: 371-399.
72. McMordie RAS. 1990. PhD thesis. The Queen's University of Belfast, Belfast, Northern Ireland.
73. Murdock D, BD Ensley, C Serdar and M Thalen. 1993. Construction of metabolic operons catalyzing the de novo biosynthesis of indigo in Escherichia coli. Bio/Technology 11: 381-386.
74. Parales JV, A Kumar, RE Parales and DT Gibson. 1996. Cloning and sequencing of the genes encoding 2-nitrotoluene dioxygenase from Pseudomonas sp JS42. Gene (in press).
75. Patel TR and DT Gibson. 1974. Purification and properties of (+)-cis-naphthalene dihydrodiol dehydrogenase of Pseudomonas putida. J Bacteriol 119: 879-888.
76. Que LJ. 1993. Oxygen activation at nonheme iron centers. In: Bioinorganic Catalysis (Reedijk J, ed), pp 347-393, Marcel Dekker, New York, NY.
77. Resnick SM and DT Gibson. 1996. Regio- and stereospecific oxidation of 9,10-dihydroanthracene and 9,10-dihydrophenanthrene by naphthalene dioxygenase: structure and absolute stereochemistry of metabolites. Appl Environ Microbiol 62: 3355-3359.
78. Resnick SM and DT Gibson. 1996. Regio- and stereospecific oxidation of fluorene, dibenzofuran and dibensothiophene by naphthalene dioxygenase from Pseudomonas sp NCIB 9816-4. Appl Environ Microbiol (in press).
79. Resnick SM and DT Gibson. 1993. Biotransformation of anisole and phenetole by aerobic hydrocarbon-oxidizing bacteria. Biodegradation 4: 195-203.
80. Resnick SM and DT Gibson. 1996. Oxidation of 6,7-dihydro-5H-benzocycloheptene by bacterial strains expressing naphthalene dioxygenase, biphenyl dioxygenase, and toluene dioxygenase yields homochiral monol or cis-diol enantiomers as major products. Appl Environ Microbiol 62: 1364-1368.
81. Resnick SM, DS Torok and DT Gibson. 1993. Oxidation of carbazole to 3-hydroxycarbazole by naphthalene 1,2-dioxygenase and biphenyl 2,3-dioxygenase. FEMS Microbiol Lett 113: 297-302.
82. 1H NMR determination of the absolute configuration and enantiomeric excess of bacterial and synthetic cis-diols. J Org Chem 60: 3546-3549.
83. Resnick SM, DS Torok, K Lee, JM Brand and DT Gibson. 1994. Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase. Appl Environ Microbiol 60:3323-3328.
84. Ribbons DW, SJC Taylor, CT Evans, SD Thomas, JT Rossiter, DA Widdowson and DJ Williams. 1990. Biodegradations yield novel intermediates for chemical synthesis. In: Biotechnology and Biodegradation (Kamely D, A Chakrabarty and GS Omenn, eds), pp 213-245, Portfolio Publishing Company, The Woodlands, TX.
85. Selifonov SA, M Grifoll, RW Eaton and PJ Chapman. 1996. Oxidation of naphthenoaromatic and methyl-substituted aromatic compounds by naphthalene 1,2-dioxygenase. Appl Environ Microbiol 62: 507-514.
86. Serdar CM and DT Gibson. 1989. Studies of nucleotide sequence homology between naphthalene-utilizing strains of bacteria. Biochem Biophys Res Commun 164: 772-779.
87. Sheldrake GN. 1992. Biologically derived arene cis-dihydrodiols as synthetic building blocks. In: Chirality in Industry: the Commercial Manufacture and Application of Optically Active Compounds (Collins AN, GN Sheldrake and J Crosby, eds), pp 127-166, John Wiley & Sons, Chichester, UK.
88. Simon MJ, TD Osslund, R Saunders, BD Ensley, S Suggs, A Harcourt, W-C Suen, DL Cruden, DT Gibson and GJ Zylstra. 1993. Sequences of genes encoding naphthalene dioxygenase in Pseudomonas putida strains G7 and NCIB 9816-4. Gene 127: 31-37.
89. Smith MR. 1990. The biodegration of aromatic hydrocarbons by bacteria. Biodegradation 1: 191-206.
90. Stabile MR. 1995. PhD thesis. Virginia Polytechnic Institute and State University, Blacksburg, VA.
91. Suen W-C. 1991. PhD thesis. The University of Iowa, Iowa City, IA.
92. Suen W-C and DT Gibson. 1993. Isolation and preliminary characterization of the subunits of the terminal component of naphthalene dioxygenase from Pseudomonas putida NCIB 9816-4. J Bacteriol 175: 5877-5881.
93. Suen W-C and DT Gibson. 1994. Recombinant Escherichia coli strains synthesize active forms of naphthalene dioxygenase and its individual α and β subunits. Gene 143: 67-71.
94. Sutherland JB, R Fatemeh, AA Kahn and CE Cerniglia. 1995. Mechanisms of polycyclic aromatic hydrocarbon degradation. In: Microbial Transformation and Degradation of Toxic Organic Chemicals (Young LY and CE Cerniglia, eds), pp 269-306, Wiley-Liss, New York.
95. Swanson PE. 1992. Microbial transformation of benzocyclobutene to benzocyclobutene-1-ol and benzocyclobutene-1-one. Appl Environ Microbiol 58: 3404-3406.
96. Torok DS, SM Resnick, JM Brand, DL Cruden and DT Gibson. 1995. Desaturation and oxygenation of 1,2-dihydronaphthalene by toluene and naphthalene dioxygenase. J Bacteriol 177: 5799-5805.
97. Torsvik V, J Goksoyr and FL Daae. 1990. High diversity in DNA of soil bacteria. Appl Environ Microbiol 56: 782-787.
98. Wackett LP, LD Kwart and DT Gibson. 1988. Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida. Biochemistry 27: 1360-1367.
99. Wende P, F-H Bernhardt and K Pfleger. 1989. Substrate-modulated reactions of putidamonooxin: the nature of the active oxygen species formed and its reaction mechanism. Eur J Biochem 181: 189-197.
100. Whited GM, JC Downie, T Hudlicky, SP Fearnley, TC Dudding, HF Olivo and D Parker. 1994. Oxidation of 2-methoxynaphthalene by toluene, naphthalene and biphenyl dioxygenases: structure and absolute stereochemistry of metabolites. Bioorg Med Chem 2: 727-734.
101. Widdowson DA and DW Ribbons. 1990. The use of substituted cyclohexadiene diols as versatile chiral synthons. Janssen Chim Acta 8: 3-9.
102. Yen K-M and IC Gunsalus. 1982. Plasmid gene organization: naphthalene/salicylate oxidation. Proc Natl Acad Sci USA 79: 874-878.
103. Yen K-M and CM Serdar. 1988. Genetics of naphthalene catabolism in pseudomonads. Crit Rev Microbiol 15: 247-267.
104. Ziffer H, K Kabuto, DT Gibson, VM Kobal and DM Jerina. 1977. The absolute stereochemistry of several cis-dihydrodiols microbially produced from substituted benzenes. Tetrahedron 33: 2491-2496.