TNT biotransformation: When chemistry confronts mineralization

Applied Microbiology and Biotechnology

Volumn 76, Issue 2, 2007, Pages 267-277

  Smets, Barth F ^a   Yin, Hong ^b   Esteve Nuñez, Abraham ^c  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b Metcalf and Eddy   (United States)

^c CENTRO DE ASTROBIOLOGÍA CSIC INTA   (Spain)

Author keywords

Biotransformation; Denitration; Nitroreductase; Old yellow enzyme; Phytoremediation; TNT

Indexed keywords

AMMONIA; BIOCHEMISTRY; DENITRIFICATION; ENZYMES; METABOLITES; REACTION KINETICS;

BIOTRANSFORMATION; NITROREDUCTION; PHYTOREMEDIATION;

AROMATIC COMPOUNDS;

AMMONIA; NITRITE; NITROGEN; NITROREDUCTASE; OXYGEN; OXYGENASE; TRINITROTOLUENE;

BIOCHEMISTRY; BIOTRANSFORMATION; ENZYME; GENETICS; IMMOBILIZATION; MICROBIAL ACTIVITY; MINERALIZATION; PHYTOREMEDIATION; REDUCTION; TRINITROTOLUENE;

BACTERIAL STRAIN; BACTERIUM; BIOTRANSFORMATION; BREATHING; CHEMISTRY; ENZYME ANALYSIS; ENZYME MECHANISM; FUNGUS; HYDROXYLATION; IMMOBILIZATION; METABOLITE; MINERALIZATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PHYTOREMEDIATION; REDUCTION; SHORT SURVEY; SOIL POLLUTION; STIMULATION; WHOLE CELL; YEAST;

BACTERIA; BIOTRANSFORMATION; NITROREDUCTASES; TRINITROTOLUENE;

EID: 34547117597     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-007-1008-7     Document Type: Short Survey

References (103)

1. Bhadra R, Wayment DG, Hughes JB, Shanks JV (1999) Confirmation of conjugation processes during TNT metabolism by axenic plant roots. Environ Sci Technol 33:446-452
2. Borch T, Inskeep WP, Harwood JA, Gerlach R (2005) Impact of ferrihydrite and anthraquinone-2,6-disulfonate on the reductive transformation of 2,4,6-trinitrotoluene by a gram-positive fermenting bacterium. Environ Sci Technol 39:7126-7133
3. Bryant C, DeLuca M (1991) Purification and characterization of an oxygen-insensitive NAD(P)H nitroreductase from Enterobacter cloacae. J Biol Chem 266:4119-4125
4. Bryant D, McCalla D, Leeksma M, Laneuville P (1981) Type I nitroreductases of Escherichia coli. Can J Microbiol 27:81-86
5. Bryant C, Hubbard L, McElroy W (1991) Cloning, nucleotide sequence, and expression of the nitroreductase gene from Enterobacter cloacae. J Biol Chem 266:4126-4130
6. Caballero A, Ramos JL (2006) A double mutant of Pseudomonas putida JLR11 deficient in the synthesis of the nitroreductase PnrA and assimilatory nitrite reductase NasB is impaired for growth on 2,4,6-trinitrotoluene (TNT). Environ Microbiol 8:1306-1310
7. Caballero A, Esteve-Nuñez A, Zylstra GJ, Ramos JL (2005a) Assimilation of nitrogen from nitrite and trinitrotoluene in Pseudomonas putida JLR11. J Bacteriol 187:396-399
8. Caballero A, Lazaro JJ, Ramos JL, Esteve-Nuñez A (2005b) PnrA, a new nitroreductase-family enzyme in the TNT-degrading strain Pseudomonas putida JLR11. Environ Microbiol 7: 1211-1219
9. Chang YY, Kwon YS, Kim SY, Lee IS, Bae B (2004) Enhanced degradation of 2,4,6-trinitrotoluene (TNT) in a soil column planted with Indian mallow (Abutilon avicennae). J Biosci Bioeng 97: 99-103
10. Claus H, Bausinger T, Lehmler I, Perret N, Fels G, Dehner U, Preuss J, Konig H (2007) Transformation of 2,4,6-trinitrotoluene (TNT) by Raoultella terrigena. Biodegradation 18:27-35
11. Dodard SG, Renoux AY, Powlowski J, Sunahara GI (2003) Lethal and subchronic effects of 2,4,6-trinitrotoluene (TNT) on Enchytraeus albidus in spiked artificial soil. Ecotoxicol Environ Saf 54:131-138
12. Esteve-Nuñez A, Ramos J (1998) Metabolism of 2,4,6-trinitrotoluene by Pseudomonas sp. JLR11. Environ Sci Technol 32:3802-3808
13. Esteve-Nuñez A, Lucchesi G, Philipp B, Schink B, Ramos JL (2000) Respiration of 2,4,6-trinitrotoluene by Pseudomonas sp. strain JLR11. J Bacteriol 182:1352-1355
14. Esteve-Nuñez A, Caballero A, Ramos JL (2001) Biological degradation of 2,4,6-trinitrotoluene. Microbiol Mol Biol Rev 65:335-352
15. Fitzpatrick TB, Amrhein N, Macheroux P (2003) Characterization of YqjM, an old yellow enzyme homolog from bacillus subtilis involved in the oxidative stress response. J Biol Chem 278(22):19891-19897
16. French CE, Nicklin S, Bruce NC (1998) Aerobic degradation of 2,4,6-trinitrotoluene by Enterobacter cloacae PB2 and by pentaerythritol tetranitrate reductase. Appl Environ Microbiol 64:2864-2868
17. French CE, Rosser SJ, Davies GJ, Nicklin S, Bruce NC (1999) Biodegradation of explosives by transgenic plants expressing pentaerythritol tetranitrate reductase. Nat Biotechnol 17:491-494
18. Frische T (2003) Ecotoxicological evaluation of in situ bioremediation of soils contaminated by the explosive 2,4,6-trinitrotoluene (TNT). Environ Pollut 121:103-113
19. Fritsche W, Scheibner K, Herre A, Hofrichter M (2000) Fungal degradation of explosives: TNT and related nitroaromatic compounds. In: Spain J, Hughes J, Knackmuss H (eds) Biodegradation of nitroaromatic compounds and explosives. Lewis, Boca Raton, FL, pp 227-233
20. Goodwin A, Kersulyte D, Sisson G, Veldhuyzen van Zanten SJ, Berg DE, Hoffman PS (1998) Metronidazole resistance in Helicobacter pylori is due to null mutations in a gene (rdxA) that encodes an oxygen-insensitive NADPH nitroreductase. Mol Microbiol 28:383-393
21. Haidour A, Ramos JL (1996) Identification of products resulting from the biological reduction of 2,4,6-trinitrotoluene, 2,4-dinitrotoluene, and 2,6-dinitrotoluene by Pseudomonas sp. Environ Sci Technol 30:2365-2370
22. Hampton ML, Sisk WE (1997) Environmental stability of windrow composting of explosives-contaminated soils. In: Tedder DW (ed) Emerging technologies in hazardous waste management IX. American Chemical Society, Washington, DC, pp 252-257
23. Hannink N, Rosser SJ, French CE, Basran A, Murray JAH, Nicklin S, Bruce NC (2001) Phytodetoxification of TNT by transgenic plants expressing a bacterial nitroreductase. Nat Biotechnol 19:1168-1172
24. Hannink NK, Rosser SJ, Bruce NC (2002) Phytoremediation of explosives. Crit Rev Plant Sci 21:511-538
25. Hawari J, Beaudet S, Halasz A, Thiboutot S, Ampleman G (2000) Microbial degradation of explosives: biotransformation versus mineralization. Appl Microbiol Biotechnol 54:605-618
26. Haynes CA, Koder RL, Miller A-F, Rodgers DW (2002) Structures of nitroreductase in three states: effects of inhibitor binding and reduction. J Biol Chem 277:11513-11520
27. Hoehamer CF, Wolfe NL, Eriksson KEL (2006a) Differences in the biotransformation of 2,4,6-trinitrotoluene (TNT) between wild and axenically grown isolates of Myriophyllum aquaticum. Int J Phytoremediat 8:107-115
28. Hoehamer CF, Wolfe NL, Eriksson KEL (2006b) Biotransformation of 2,4,6-trinitrotoluene (TNT) by the fungus Fusarium oxysporum. Int J Phytoremediat 8:95-105
29. Homma-Takeda S, Hiraku Y, Ohkuma Y, Oikawa S, Murata M, Ogawa K, Iwamuro T, Li S, Sun GF, Kumagai Y, Shimojo N, Kawanishi S (2002) 2,4,6-Trinitrotoluene- induced reproductive toxicity via oxidative DNA damage by its metabolite. Free Radic Res 36:555-566
30. Hughes JB, Wang C, Yesland K, Richardson A, Bhadra R, Bennett G, Rudolph F (1998) Bamberger rearrangement during TNT metabolism by Clostridium acetobutylicum. Environ Sci Technol 32:494-500
31. Jain MR, Zinjarde SS, Deobagkar DD, Deobagkar DN (2004) 2,4,6-Trinitrotoluene transformation by a tropical marine yeast, Yarrowia lipolytica NCIM 3589. Mar Pollut Bull 49:783-788
32. Johnson GR, Smets BF, Spain JC (2001) Oxidative transformation of aminodinitrotoluene isomers by multicomponent dioxygenases. Appl Environ Microbiol 67:5460-5466
33. Keenan BG, Wood TK (2006) Orthric Rieske dioxygenases for degrading mixtures of 2,4-dinitrotoluene/naphthalene and 2-amino-4,6-dinitrotoluene/4- amino-2,6-dinitrotoluene. Appl Microbiol Biotechnol 73:827-838
34. Keenan BG, Leungsakul T, Smets BF, Mori M-A, Henderson DE, Wood TK (2005) Protein engineering of the archetypal nitroarene dioxygenase of Ralstonia sp. strain U2 for activity on aminonitrotoluenes and dinitrotoluenes through alpha-subunit residues Leucine 225, Phenylalanine 350, and Glycine 407. J Bacteriol 187:3302-3310
35. Khan H, Harris RJ, Barna T, Craig DH, Bruce NC, Munro AW, Moody PCE, Scrutton NS (2002) Kinetic and structural basis of reactivity of pentaerythritol tetranitrate reductase with NADPH, 2-cyclohexenone, nitroesters, and nitroaromatic explosives. J Biol Chem 277:21906-21912
36. Kim HY, Song HG (2000) Comparison of 2,4,6-trinitrotoluene degradation by seven strains of white rot fungi. Curr Microbiol 41:317-320
37. Kim HY, Song HG (2003) Transformation and mineralization of 2,4,6-trinitrotoluene by the white rot fungus Irpex lacteus. Appl Microbiol Biotechnol 61:150-156
38. Kim HY, Song H-G (2005) Purification and characterization of NAD(P)H-dependent nitroreductase I from Klebsiella sp. C1 and enzymatic transformation of 2,4,6-trinitrotoluene. Appl Microbiol Biotechnol 68:766-773
39. Kim HY, Bennett GN, Song HG (2002) Degradation of 2,4,6-trinitrotoluene by Klebsiella sp isolated from activated sludge. Biotechnol Lett 24:2023-2028
40. Knicker H, Achtnich C, Lenke H (2001) Solid-state nitrogen-15 nuclear magnetic resonance analysis of biologically reduced 2,4,6-trinitrotoluene in a soil slurry remediation. J Environ Qual 30:403-410
41. Koder RL, Miller AF (1998) Steady-state kinetic mechanism, stereospecificity, substrate and inhibitor specificity of Enterobacter cloacae nitroreductase. Biochim Biophys Acta 1387:395-405
42. Kumagai Y, Wakayama T, Li S, Shinohara A, Iwamatsu A, Sun G, Shimojo N (2000) [zeta]-Crystallin catalyzes the reductive activation of 2,4,6-trinitrotoluene to generate reactive oxygen species: a proposed mechanism for the induction of cataracts. FEBS Lett 478:295-298
43. Kurinenko BM, Denivarova NA, Yakovleva GY (2005) Sensitivity of various Escherichia coli strains to 2,4,6-trinitrotoluene. Appl Biochem Microbiol 41:47-50
44. Kutty R, Bennett GN (2005) Biochemical characterization of trinitrotoluene transforming oxygen-insensitive nitroreductases from Clostridium acetobutylicum ATCC 824. Arch Microbiol 184(3):158-167
45. Kutty R, Bennett GN (2006) Studies on inhibition of transformation of 2,4,6-trinitrotoluene catalyzed by Fe-only hydrogenase from Clostridium acetobutylicum. J Ind Microbiol Biotechnol 33:368-376
46. Lachance B, Renoux AY, Sarrazin M, Hawari J, Sunahara GI (2004) Toxicity and bioaccumulation of reduced TNT metabolites in the earthworm Eisenia andrei exposed to amended forest soil. Chemos 55:1339-1348
47. Lei B, Liu M, Huang S, Tu SC (1994) Vibrio harveyi NADPH-flavin oxidoreductase: cloning, sequencing and overexpression of the gene and purification and characterization of the cloned enzyme. J Bacteriol 176:3552-3558
48. Leung KH, Yao M, Stearns R, Chiu S-HL (1995) Mechanism of bioactivation and covalent binding of 2,4,6-trinitrotoluene. Chem Biol Interact 97:37-51
49. Lewis TA, Ederer MM, Crawford RL, Crawford DL (1997) Microbial transformation of 2,4,6-trinitrotoluene. J Ind Microbiol Biotechnol 18:89-96
50. Lewis TA, Newcombe DA, Crawford RL (2004) Bioremediation of soils contaminated with explosives. J Environ Manag 70:291-307
51. Martin JL, Comfort SD, Shea PJ, Kokjohn TA, Drijber RA (1997) Denitration of 2,4,6-trinitrotoluene by Pseudomonas savastanoi. Can J Microbiol 43:447-455
52. Meah Y, Brown BJ, Chakraborty S, Massey V (2001) Old yellow enzyme: reduction of nitrate esters, glycerin trinitrate, and propylene 1,2-dinitrate. PNAS 98:8560-8565
53. Mezzari MP, Walters K, Jelinkova M, Shih MC, Just CL, Schnoor JL (2005) Gene expression and microscopic analysis of arabidopsis exposed to chloroacetanilide herbicides and explosive compounds. A phytoremediation approach. Plant Physiol 138:858-869
54. Nokhbeh MR, Boroumandi S, Pokorny N, Koziarz P, Paterson ES, Lambert IB (2002) Identification and characterization of SnrA, an inducible oxygen-insensitive nitroreductase in Salmonella enterica serovar Typhimurium TA1535. Mutat Res 508:59-70
55. Nyanhongo GS, Schroeder M, Steiner W, Gubitz GM (2005) Biodegradation of 2,4,6-trinitrotoluene (TNT): An enzymatic perspective. Biocatal Biotransform 23:53-69
56. Nyanhongo GS, Erlacher A, Schroeder M, Gubitz GA (2006) Enzymatic immobilization of 2,4,6-trinitrotoluene (TNT) biodegradation products onto model humic substances. Enzyme Microb Technol 39:1197-1204
57. Oh BT, Shea PJ, Drijber RA, Vasilyeva GK, Sarath G (2003) TNT biotransformation and detoxification by a Pseudomonas aeruginosa strain. Biodegradation 14:309-319
58. Orville AM, Manning L, Blehert DS, Fox BG, Chambliss GH (2004a) Crystallization and preliminary analysis of xenobiotic reductase B from Pseudomonas fluorescens I-C. Acta Crystallogr D Biol Crystallogr 60:1289-1291
59. Orville AM, Manning L, Blehert DS, Studts JM, Fox BG, Chambliss GH (2004b) Crystallization and preliminary analysis of xenobiotic reductase A and ligand complexes from Pseudomonas putida II-B. Acta Crystallogr D Biol Crystallogr 60:957-961
60. Pak JW, Knoke KL, Noguera DR, Fox BG, Chambliss GH (2000) Transformation of 2,4,6-trinitrotoluene by purified xenobiotic reductase B from Pseudomonas fluorescens I-C. Appl Environ Microbiol 66:4742-4750
61. Park HS, Kim HS (2000) Identification and characterization of the nitrobenzene catabolic plasmids pNB1 and pNB2 in Pseudomonas putida HS12. J Bacteriol 182:573-580
62. Park HJ, Reiser CO, Kondruweit S, Erdmann H, Schmid RD, Sprinzl M (1992) Purification and characterization of a NADH oxidase from the thermophile Thermus thermophilus HB8. Eur J Biochem 205:881-885
63. Park C, Kim T-H, Kim S, Lee J, Kim S-W (2003a) Bioremediation of 2,4,6-trinitrotoluene contaminated soil in slurry and column reactors. J Biosci Bioeng 96:429-433
64. Park C, Kim TH, Kim S, Kim SW, Lee J, Kim SH (2003b) Optimization for biodegradation of 2,4,6-trinitrotoluene (TNT) by Pseudomonas putida. J Biosci Bioeng 95:567-571
65. Paterson ES, Boucher SE, Lambert IB (2002) Regulation of the nfsA gene in Escherichia coli by SoxS. J Bacteriol 184:51-58
66. Peterson FJ, Mason RP, Horspian J, Holtzman JL (1979) Oxygen-sensitive and insensitive nitroreduction by Escherichia coli and rat hepatic microcosomes. J Biol Chem 254:4009-4014
67. Popesku JT, Singh A, Zhao JS, Hawari J, Ward OP (2003) High TNT-transforming activity by a mixed culture acclimated and maintained on crude-oil-containing media. Can J Microbiol 49:362-366
68. Preuss A, Fimpel J, Diekert G (1993) Anaerobic transformation of 2,4,6-trinitrotoluene (TNT). Arch Microbiol 159:345-353
69. Ramos JL, Gonzalez-Perez MM, Caballero A, van Dillewijn P (2005) Bioremediation of polynitrated aromatic compounds: plants and microbes put up a fight. Curr Opin Biotechnol 16:275-281
70. Rau J, Stolz A (2003) Oxygen-insensitive nitroreductases NfsA and NfsB of Escherichia coli function under anaerobic conditions as lawsone-dependent azo reductases. Appl Environ Microbiol 69:3448-3455
71. Riefler RG, Smets BF (2000) Enzymatic reduction of 2,4,6-trinitrotoluene and related nitroarenes: kinetics linked to one-electron redox potentials. Environ Sci Technol 34:3900-3906
72. Riefler RG, Smets BF (2002) NAD(P)H:flavin mononucleotide oxidoreductase inactivation during 2,4,6-trinitrotoluene reduction. Appl Environ Microbiol 68:1690-1696
73. Robertson BK, Jjemba PK (2005) Enhanced bioavailability of sorbed 2,4,6-trinitrotoluene (TNT) by a bacterial consortium. Chemosphere 58:263-270
74. Robidoux PY, Bardai G, Paquet L, Ampleman G, Thiboutot S, Hawari J, Sunahara GI (2003) Phytotoxicity of 2,4,6-trinitrotoluene (TNT) and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) in spiked artificial and natural forest soils. Arch Environ Contam Toxicol 44:198-209
75. Sarlauskas J, Nemeikaite-Ceniene A, Anusevicius Z, Miseviciene L, Julvez MM, Medina M, Gomez-Moreno C, Cenas N (2004) Flavoenzyme-catalyzed redox cycling of hydroxylamino- and amino metabolites of 2,4,6-trinitrotoluene: implications for their cytotoxicity. Arch Biochem Biophys 425:184-192
76. Schloss PD, Handelsman J (2003) Biotechnological prospects from metagenomics. Curr Opin Biotechnol 14:303-310
77. Schoenmuth BW, Pestemer W (2004) Dendroremediation of trinitrotoluene (TNT). Part 2: fate of radio-labelled TNT in trees. Environ Sci Pollut Res Int 11:331-339
78. Schrader PS, Hess TF (2004) Coupled abiotic-biotic mineralization of 2,4,6-trinitrotoluene (TNT) in soil slurry. J Environ Qual 33:1202-1209
79. Sens C, Scheidemann P, Werner D (1999) The distribution of 14C-TNT in different biochemical compartments of the monocotyledonous Triticum aestivum. Environ Pollut 104:113-119
80. Somerville CC, Nishino SF, Spain JC (1995) Purification and characterization of nitrobenzene nitroreductase from Pseudomonas pseudoalcaligenes JS45. J Bacteriol 177:3837-3842
81. Spain J, Hughes JB, Knackmuss H-J (2000) Biodegradation of nitroaromatic compounds and explosives. Lewis, Boca Raton, FL
82. Stenuit B, Eyers L, Rozenberg R, Habib-Jiwan JL, Agathos SN (2006) Aerobic growth of Escherichia coli with 2,4,6-trinitrotoluene (TNT) as the sole nitrogen source and evidence of TNT denitration by whole cells and cell-free extracts. Appl Environ Microbiol 72:7945-7948
83. Subramanian M, Oliver DJ, Shanks JV (2006) TNT phytotransformation pathway characteristics in arabidopsis: role of aromatic hydroxylamines. Biotechnol Prog 22:208-216
84. Symons ZC, Bruce NC (2006) Bacterial pathways for degradation of nitroaromatics. Nat Prod Rep 23:845-850
85. Talmage SS, Opresko DM, Maxwell CJ, Welsh CJ, Cretella FM, Reno PH, Daniel FB (1999) Nitroaromatic munition compounds: environmental effects and screening values. Rev Environ Contam Toxicol 161:1-156
86. Thiele S, Fernandes E, Bollag JM (2002) Enzymatic transformation and binding of labeled 2,4,6-trinitrotoluene to humic substances during an anaerobic/aerobic incubation. J Environ Qual 31:437-444
87. Thorn KA, Pennington JC, Hayes CA (2002) M-15 NMR investigation of the reduction and binding of TNT in an aerobic bench scale reactor simulating windrow composting. Environ Sci Technol 36:3797-3805
88. Tront JM, Hughes JB (2005) Oxidative microbial degradation of 2,4,6-trinitrotoluene via 3-methyl-4,6-dinitrocatechol. Environ Sci Technol 39:4540-4549
89. Vila M, Pascal-Lorber S, Rathahao E, Debrauwer L, Canlet C, Laurent F (2005) Metabolism of [14C]-2,4,6-trinitrotoluene in tobacco cell suspension cultures. Environ Sci Technol 39:663-672
90. Vorbeck C, Lenke H, Fischer P, Knackmuss HJ (1994) Identification of a hydride-Meisenheimer complex as a metabolite of 2,4,6-trinitrotoluene by a Mycobacterium strain. J Bacteriol 176:932-934
91. Wang C-J, Thiele S, Bollag J-M (2002) Interaction of 2,4,6- trinitrotoluene (TNT) and 4-amino-2,6-dinitrotoluene with humic monomers in the presence of oxidative enzymes. Arch Environ Contam Toxicol 42:1-8
92. Wang C, Lyon DY, Hughes JB, Bennett GN (2003) Role of hydroxylamine intermediates in the phytotransformation of 2,4,6-trinitrotoluene by Myriophyllum aquaticum. Environ Sci Technol 37:3595-3600
93. Watanabe M, Ishidate M Jr, Nohmi T (1990) Nucleotide sequence of Salmonella typhimurium nitroreductase gene. Nucleic Acids Res 18:1059
94. Watrous MM, Clark S, Kutty R, Huang S, Rudolph FB, Hughes JB, Bennett GN (2003) 2,4,6-trinitrotoluene reduction by an Fe-only hydrogenase in Clostridium acetobutylicum. Appl Environ Microbiol 69:1542-1547
95. Weiss M, Geyer R, Gunther T, Kaestner M (2004) Fate and stability of C-14-labeled 2,4,6-trinitrotoluene in contaminated soil following microbial bioremediation processes. Environ Toxicol Chem 23:2049-2060
96. Williams RE, Rathbone DA, Scrutton NS, Bruce NC (2004) Biotransformation of explosives by the old yellow enzyme family of flavoproteins. Appl Environ Microbiol 70:3566-3574
97. Yin H, Wood TK, Smets BF (2004) Reductive transformation of TNT by Escherichia coli: pathway description. Appl Microbiol Biotechnol 67:397-404
98. Yin H, Wood TK, Smets BF (2005) Reductive transformation of TNT by Escherichia coli resting cells: kinetic analysis. Appl Microbiol Biotechnol 69:326-334
99. Yoon JM, Van Aken B, Schnoor JL (2006) Leaching of contaminated leaves following uptake and phytoremediation of RDX, HMX, and TNT by poplar. Int J Phytoremediat 8:81-94
100. Zaripov SA, Naumov AV, Abdrakhmanova JF, Garusov AV, Naumova RP (2002) Models of 2,4,6-trinitrotoluene (TNT) initial conversion by yeasts. FEMS Microbiol Lett 217:213-217
101. Zenno S, Saigo K, Kanoh H, Inouye S (1994) Identification of the gene encoding the major NAD(P)H-flavin oxidoreductase of the bioluminescent bacterium Vibrio fischeri ATCC 7744. J Bacteriol 176:3536-3543
102. Zenno S, Koike H, Tanokura M, Saigo K (1996a) Conversion of NfsB, a minor Escherichia coli nitroreductase, to a flavin reductase similar in biochemical properties to FRase I, the major flavin reductase in Vibrio fischeri, by a single amino acid substitution. J Bacteriol 178:4731-4733
103. Zenno S, Koike H, Kumar A, Jayaraman R, Tanokura M, Saigo K (1996b) Biochemical characterization of NfsA, the Escherichia coli major nitroreductase exhibiting a high amino acid sequence homology to Frp, a Vibrio harveyi flavin oxidoreductase. J Bacteriol 178:4508-4514