Naphthalene 1,2-Dioxygenase Reactions

[Naphthalene 1,2-Dioxygenase] [Naphthalene] [1-Methylnaphthalene] [2-Methylnaphthalene] [Fluorene] [Ethylbenzene] [Mordant Yellow 3] [Anthracene] [Dibenzothiophene] [BBD Main Menu]

These tables list many of the reactions catalyzed by the versatile enzyme naphthalene 1,2-dioxygenase, EC 1.14.12.12, and a literature reference for each reaction. The organization of this table and many reactions are based on a review article: Resnick SM, Lee K, Gibson DT "Diverse reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp strain NCIB 9816" J Ind Microbiol (1996) 17: 438-57. [Reaction] links to a EAWAG-BBD reaction; [Abstract] links to a PubMed abstract. If there are any reactions we have missed, please let us know.

These 76 reactions are organized into five major groups (number in each group or subgroup):

    A. Dioxygenation Reactions (31)
          Acts on aromatic hydrocarbons (12)
          Acts on substituted aromatic compounds (14)
          Acts on heterocyclic aromatic compounds (5)

    B. Monooxygenation Reactions (24)

    C. Desaturation Reactions (7)

    D. O- and N-Dealkylation Reactions (5)

    E. Sulfoxidation Reactions (9)

References

A. Dioxygenation Reactions
Acts on aromatic hydrocarbons
No. Reactions Refs
1. Naphthalene ----> (+)-cis-(1R,2S)-Dihydroxy-1,2-dihydronaphthalene [Reaction] [1]
2. Indene ----> cis-(1R,2S)-Indandiol [2]
3. 1,2-Dihydronaphthalene ----> (-)-cis-(1R,2S)-Dihydroxy-1,2,3,4-tetrahydronaphthalene [3]
4. Benzocyclohept-1-ene ----> (-)-cis-(1R,2S)-Dihydroxybenzocycloheptane [4]
5. Biphenyl ----> (+)-(2R,3S)-Dihydro-2,3-dihydroxybiphenyl [5]
6. Anthracene ----> (+)-cis-(1R,2S)-Dihydroxy-1,2-dihydroanthracene [Reaction] [6]
7. 9,10-Dihydroanthracene ----> (+)-cis-(1R,2S)-Dihydroxy-1,2,9,10-tetrahydroanthracene [7]
8. Phenanthrene ----> (+)-cis-(3S,4R)-Dihydroxy-3,4-dihydrophenanthrene [6]
9. Phenanthrene ----> (+)-cis-(1S,2R)-Dihydroxy-1,2-dihydrophenanthrene [6]
10. Acenaphthylene ----> cis-Acenaphthene-1,2-diol [Reaction] [8]
11. 9,10-Dihydrophenanthrene ----> cis-(3S,4R)-Dihydroxy-3,4,9,10-tertrahydrophenanthrene [7]
12. Fluorene ----> cis-(3S,4R)-Dihydroxy-3,4-dihydrofluorene [Reaction] [9]
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Acts on substituted aromatic compounds
No. Reactions Refs
13. Styrene ----> (R)-1-Phenyl-1,2-Ethanediol [10]
14. (1R)-Indenol ----> cis-1,2,3-Indantriol [11]
15. 2-Methoxynaphthalene ----> (+)-(1R,2S)-Dihydroxy-7-methoxy-1,2-dihydronaphthalene [12]
16. 2-Methoxynaphthalene ----> (+)-(1R,2S)-Dihydroxy-6-methoxy-1,2-dihydronaphthalene [12]
17. 2-Naphthoic acid ----> (+)-cis-1,2-Dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid [13]
18. 2,6-Dimethylnaphthalene ----> (+)-cis-1,2-Dihydro-(1R,2S)-dihydroxy-3,7-dimethylnaphthalene [14]
19. 2,3-Dimethylnaphthalene ----> (+)-cis-1,2-Dihydro-(1R,2S)-dihydroxy-6,7-dimethylnaphthalene [14]
20. 1-Carbomethoxynaphthalene ----> cis-3,4-Dihydro-(2S)-hydroxynaphthalene-8,(1R)-lactone [14]
21. 1-Methylnaphthalene ----> cis-1,2-Dihydro-(1R,2S)-dihydroxy-8-methylnaphthalene [Reaction] [14]
22. 1-Methoxynaphthalene ----> cis-1,2-Dihydro-(1R,2S)-dihydroxy-5-methoxynaphthalene [14]
23. 2-Nitronaphthalene ----> cis-1,2-Dihydro-(1R,2S)-dihydroxy-7-nitronaphthalene [14]
24. 2-Hydroxymethylnaphthalene---->cis-1,2-Dihydroxy-1,2-dihydro-7-hydroxymethyl naphthalene [Reaction] [26]
25. 2-Methylnaphthalene---->cis-1,2-Dihydroxy-1,2-dihydro-7-methylnaphthalene [Reaction] [26]
26. 6-Amino-2-naphthalenesulfonic acid ---->6-Amino-1-hydro-cis-1,2-dihydroxy-2-naphthylsulfonic acid [Reaction] [27]
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Acts on heterocyclic aromatic compounds
No. Reactions Refs
27. Indole ----> Indigo [15]
28. Dibenzo-1,4-dioxin ----> cis-1,2-Dihydroxy-1,2-dihydrodibenzo[1,4]dioxan [16]
29. Dibenzothiophene ----> (+)-cis-(1R,2S)-Dihydroxy-1,2-dihydrodibenzothiophene [Reaction] [9]
30. Dibenzofuran ----> cis-1,2-Dihydroxy-1,2-dihydrodibenzofuran [9]
31. Dibenzofuran ----> cis-3,4-Dihydroxy-3,4-dihydrodibenzofuran [9]
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B. Monooxygenation Reactions
No. Reactions Refs
32. Benzocyclobutene ----> Benzocyclobutene-1-ol [17]
33. Indan ----> (+)-(1S)-Indanol [18]
34. Indene ---->(+)- (1S)-Indenol [19]
35. 1-Indanone ----> (R)-3-Hydroxy-1-indanone [20]
36. 1-Indanone ----> (R)-2-Hydroxy-1-indanone [20]
37. 2-Indanone ----> (S)-2-Hydroxy-1-indanone [20]
38. (1R)-Indanol ----> cis-(1R,3S)-Indan-1,3-diol [11]
39. (1S)-Indanol ----> trans-(1S,3R)-Indan-1,3-diol [11]
40. Fluorene ----> 9-Fluorenol [Reaction] [9]
41. Acenaphthene ----> 1-Acenaphthenol [8]
42. Acenaphthen-1-ol ----> cis-Acenaphthene-1,2-diol [8]
43. Acenaphthen-1-ol ----> trans-Acenaphthene-1,2-diol [8]
44. 9,10-Dihydrophenanthrene ----> (+)-9S-Hydroxy-9,10-dihydrophenanthrene [7]
45. Toluene ----> Benzyl alcohol [21]
46. Ethylbenzene ----> (S)-1-Phenethyl alcohol [Reaction] [21]
47. (S)-1-Phenethyl alcohol ----> Acetophenone [Reaction] [21]
48. Acetophenone ---->2-Hydroxy-acetophenone [Reaction] [21]
49. 1,2,4-Trimethylbenzene ----> 2,4-Dimethylbenzoic alcohol [8]
50. 1,2,4-Trimethylbenzene ----> 3,4-Dimethylbenzoic alcohol [8]
51. 1,2,4-Trimethylbenzene ----> 2,5-Dimethylbenzoic alcohol [8]
52. 1,2,4-Trimethylbenzene ----> 1,2-bis(Hydroxymethyl)-4-methylbenzene [8]
53. 1,2,4-Trimethylbenzene ----> 1,4(3)-bis(Hydroxymethyl)-3(4)-methylbenzene [8]
54. 3-Methylbenzothiophene ----> 3-Hydroxymethylbenzothiophene [8]
55. Carbazole ----> 3-Hydroxycarbazole [22]
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C. Desaturation Reactions
No. Reactions Refs
56. Indan ----> Indene [19]
57. 1,2-Dihydronaphthalene ----> Naphthalene [3]
58. Indoline ----> Indole [5]
59. Phenetole ----> Ethenyloxybenzene [23]
60. Ethylbenzene ----> Styrene [Reaction] [21]
61. (1R)-Indanol ----> (1S)-Indenol [11]
62. (1S)-Indanol ----> (1R)-Indenol [11]
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D. O- and N-Dealkylation Reactions
No. Reactions Refs
63. Anisole ----> Phenol [23]
64. Phenetole ----> Phenol [23]
65. N-Methylindole ----> Indole [5]
66. N-Methylaniline ----> Aniline [5]
67. N,N-Dimethylaniline ----> Aniline [5]
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E. Sulfoxidation Reactions
No. Reactions Refs
68. Methyl phenyl sulfide ----> Methyl phenyl (S)-sulfoxide [24]
69. Ethyl phenyl sulfide ----> Ethyl phenyl (S)-sulfoxide [24]
70. Methyl p-tolyl sulfide ----> Methyl p-tolyl (S)-sulfoxide [24]
71. p-Methoxyphenyl methyl sulfide ----> p-Methoxyphenyl methyl (S)-sulfoxide [24]
72. Methyl p-nitrophenyl sulfide ----> Methyl p-nitrophenyl (S)-sulfoxide [24]
73. 2-Methylbenzo-1,3-dithiole ----> cis-(1R,2S)-2-Methylbenzodithiole sulfoxide [25]
74. 2-Methylbenzo-1,3-dithiole ----> trans-(1R,2R)-2-Methylbenzodithiol sulfoxide [25]
75. 3-Methylbenzothiophene ----> 3-Methylbenzothiophene sulfoxide [8]
76. Dibenzothiophene ----> Dibenzothiophene sulfoxide [9]
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References ([Abstract] links to a PubMed abstract)

  1. Jeffrey AM, Yeh HJ, Jerina DM, Patel TR, Davey JF, Gibson DT Biochemistry (1975) 14(3): 575-84.[Abstract]

  2. Gibson DT, Resnick SM, Lee K, Brand JM, Torok DS, Wackett LP, Schocken MJ, Haigler BE J Bacteriol (1995) 177(10): 2615-21. [Abstract]

  3. Torok DS, Resnick SM, Brand JM, Cruden DL, Gibson DT J Bacteriol (1995) 177(20): 5799-805. [Abstract]

  4. Resnick SM, Gibson DT Appl Environ Microbiol (1996) 62(4): 1364-8. [Abstract]

  5. Resnick SM, Lee K, Gibson DT J Ind Microbiol (1996) 17: 438-57.

  6. Jerina DM, Selander H, Yagi H, Wells MC, Davey JF, Mahadevan V, Gibson DT J Am Chem Soc (1976) 98: 5988-96. [Abstract]

  7. Resnick SM, Gibson DT Appl Environ Microbiol (1996) 62(9): 3355-9. [Abstract]

  8. Selifonov SA, Grifoll M, Eaton RW, Chapman PJ Appl Environ Microbiol (1996) 62: 507-14. [Abstract]

  9. Resnick SM, Gibson DT Appl Environ Microbiol (1996) 62(11): 4073-80. [Abstract]

  10. Lee K, Gibson DT J Bacteriol (1996) 178(11): 3353-6. [Abstract]

  11. Lee K, Resnick SM, Gibson DT Appl Environ Microbiol (1997) 63(5): 2067-70. [Abstract]

  12. Whited GM, Downie JC, Hudlicky T, Fearnley SP, Dudding TC, Olivo HF, Parker D Bioorg Med Chem (1994) 2(7): 727-34. [Abstract]

  13. Knackmuss HJ, Beckmann W, Otting W Angew Chem Int Ed Engl (1976) 15(9): 549. [Abstract]

  14. Bestetti G, Bianchi D, Bosetti A, Gennaro P, Galli E, Leoni B, Pelizzoni F, Sello G Appl Microbiol Biotechnol (1995) 44: 306-13.

  15. Ensley BD, Ratzkin BJ, Osslund TD, Simon MJ, Wackett LP, Gibson DT Science (1983) 222(4620): 167-9. [Abstract]

  16. Klecka GM, Gibson DT Biochem J (1979) 180(3): 639-45. [Abstract]

  17. Swanson PE. Appl Environ Microbiol (1992) 58: 3404-06.[Abstract]

  18. Wackett LP, Kwart LD, Gibson DT Biochemistry (1988) 27(4): 1360-7. [Abstract]

  19. Gibson DT, Resnick SM, Lee K, Brand JM, Torok DS, Wackett LP, Schocken MJ, Haigler BE J Bacteriol (1995) 177(10): 2615-21. [Abstract]

  20. Resnick SM, Torok DS, Lee K, Brand JM, Gibson DT Appl Environ Microbiol (1994) 60(9): 3323-8. [Abstract]

  21. Lee K, Gibson DT Appl Environ Microbiol (1996) 62(9): 3101-6. [Abstract]

  22. Resnick SM, Torok DS, Gibson DT FEMS Microbiol Lett (1993) 113(3): 297-302. [Abstract]

  23. Resnick SM, Gibson DT Biodegradation (1993) 4: 195-203.

  24. Lee K, Brand JM, Gibson DT Biochem Biophys Res Commun (1995) 212(1): 9-15. [Abstract]

  25. Allen CCR, Boyd DR, Dalton H, Sharma ND, Haughey SA, McMordie RAS, McMurry BT, Sheldrake GN, Sproule K J Chem Soc Chem Commun (1995) 119-120.

  26. Mahajan MC, Phale PS, Vaidyanathan CS Arch Microbiol (1994) 161(5):425-33. [Abstract]

  27. Haug W, Schmidt A, Nortemann B, Hempel DC, Stolz A, Knackmuss HJ Appl Environ Microbiol (1991) 57(11): 3144-9. [Abstract]


[Naphthalene 1,2-Dioxygenase] [Naphthalene] [1-Methylnaphthalene] [2-Methylnaphthalene] [Fluorene] [Ethylbenzene] [Mordant Yellow 3] [Anthracene] [Dibenzothiophene] [BBD Main Menu]

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