Directed evolution of aniline dioxygenase for enhanced bioremediation of aromatic amines

Applied Microbiology and Biotechnology

Volumn 81, Issue 6, 2009, Pages 1063-1070

  Ang, Ee Lui ^a,b   Obbard, Jeffrey P ^b   Zhao, Huimin ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Aniline dioxygenase; Bioremediation; Random mutagenesis; Saturation mutagenesis; Substrate specificity

Indexed keywords

ACINETOBACTER SP; AROMATIC AMINES; CARCINOGENIC AROMATIC AMINES; DIOXYGENASE ENZYMES; DIRECTED EVOLUTIONS; ENHANCED BIOREMEDIATION; HEME IRONS; RANDOM MUTAGENESIS; SATURATION MUTAGENESIS; SUBSTRATE SPECIFICITY; WIDER RANGES; WILD TYPES;

AMINATION; AMINES; ANILINE; AROMATIC COMPOUNDS; BIODEGRADATION; BIOREMEDIATION; BIOTECHNOLOGY; ENZYMES; MUTAGENESIS; NEGATIVE IONS; ORGANIC COMPOUNDS; POLLUTION; PORPHYRINS; RANDOM PROCESSES; SUBSTRATES;

ENZYME ACTIVITY;

BACTERIUM; BIOREMEDIATION; CARCINOGEN; ENZYME ACTIVITY; EVOLUTION; MUTATION; SATURATION;

ACINETOBACTER; AMINES; ANILINE COMPOUNDS; BIODEGRADATION, ENVIRONMENTAL; DIRECTED MOLECULAR EVOLUTION; DNA MUTATIONAL ANALYSIS; MODELS, MOLECULAR; MUTAGENESIS; MUTANT PROTEINS; MUTATION, MISSENSE; OXYGENASES; PROTEIN STRUCTURE, TERTIARY; SUBSTRATE SPECIFICITY;

ACINETOBACTER SP.;

EID: 58149147461     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-008-1710-0     Document Type: Article

References (36)

1. EL Ang JP Obbard HM Zhao 2007 Probing the molecular determinants of aniline dioxygenase substrate specificity by saturation mutagenesis FEBS J 274 928 939
2. S Beil JR Mason KN Timmis DH Pieper 1998 Identification of chlorobenzene dioxygenase sequence elements involved in dechlorination of 1,2,4,5- tetrachlorobenzene J Bacteriol 180 5520 5528
3. EM Bomhard BA Herbold 2005 Genotoxic activities of aniline and its metabolites and their relationship to the carcinogenicity of aniline in the spleen of rats Crit Rev Toxicol 35 783 835
4. TDH Bugg CJ Winfield 1998 Enzymatic cleavage of aromatic rings: mechanistic aspects of the catechol dioxygenases and later enzymes of bacterial oxidative cleavage pathways Nat Prod Rep 15 513 530
5. X Dong S Fushinobu E Fukuda T Terada S Nakamura K Shimizu H Nojiri T Omori H Shoun T Wakagi 2005 Crystal structure of the terminal oxygenase component of cumene dioxygenase from Pseudomonas fluorescens IP01 J Bacteriol 187 2483 2490
6. ME Essington 1994 Adsorption of aniline and toluidines on montmorillonite Soil Sci 158 181 188
7. SL Fuenmayor M Wild AL Boyes PA Williams 1998 A gene cluster encoding steps in conversion of naphthalene to gentisate in Pseudomonas sp. strain U2 J Bacteriol 180 2522 2530
8. Y Furusawa V Nagarajan M Tanokura E Masai M Fukuda T Senda 2004 Crystal structure of the terminal oxygenase component of biphenyl dioxygenase derived from Rhodococcus sp. strain RHA1 J Mol Biol 342 1041 1052
9. Grayson M, Eckroth D, Mark HF, Othmer DF, Overberger CG, Seaborg GT (1984) Kirk-Othmer encyclopedia of chemical technology, vol. 2, 3rd edn. Wiley, New York, pp 309-375
10. B Kauppi K Lee E Carredano RE Parales DT Gibson H Eklund S Ramaswamy 1998 Structure of an aromatic-ring-hydroxylating dioxygenase-naphthalene 1,2-dioxygenase Structure 6 571 586
11. BG Keenan T Leungsakul BF Smets TK Wood 2004 Saturation mutagenesis of Burkholderia cepacia R34 2,4-dinitrotoluene dioxygenase at DntAc valine 350 for synthesizing nitrohydroquinone, methylhydroquinone, and methoxyhydroquinone Appl Environ Microbiol 70 3222 3231
12. BG Keenan T Leungsakul BF Smets MA Mori DE Henderson TK Wood 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
13. T Kumamaru H Suenaga M Mitsuoka T Watanabe K Furukawa 1998 Enhanced degradation of polychlorinated biphenyls by directed evolution of biphenyl dioxygenase Nat Biotechnol 16 663 666
14. Q Liang M Takeo M Chen W Zhang Y Xu M Lin 2005 Chromosome-encoded gene cluster for the metabolic pathway that converts aniline to TCA-cycle intermediates in Delftia tsuruhatensis AD9 Microbiology 151 3435 3446
15. CD Lyons S Katz R Bartha 1984 Mechanisms and pathways of aniline elimination from aquatic environments Appl Environ Microbiol 48 491 496
16. SB Markowitz K Levin 2004 Continued epidemic of bladder cancer in workers exposed to ortho-toluidine in a chemical factory J Occup Environ Med 46 154 160
17. GB Michaels DL Lewis 1985 Sorption and toxicity of azo and triphenylmethane dyes to aquatic microbial populations Environ Toxicol Chem 4 45 50
18. GB Michaels DL Lewis 1986 Microbial transformation rates of azo and triphenylmethane dyes Environ Toxicol Chem 5 161 166
19. FJ Mondello 1989 Cloning and expression in Escherichia coli of Pseudomonas strain LB400 genes encoding polychlorinated biphenyl degradation J Bacteriol 171 1725 1732
20. KL Morley RJ Kazlauskas 2005 Improving enzyme properties: when are closer mutations better? Trends Biotechnol 23 231 237
21. S Murakami T Hayashi T Maeda S Takenaka K Aoki 2003 Cloning and functional analysis of aniline dioxygenase gene cluster, from Frateuria species ANA-18, that metabolizes aniline via an ortho-cleavage pathway of catechol Biosci Biotechnol Biochem 67 2351 2358
22. T Nohmi R Miyata K Yoshikawa M Nakadate M Ishidate Jr 1983 Metabolic activation of 2,4-xylidine and its mutagenic metabolite Biochem Pharmacol 32 735 738
23. RE Parales SM Resnick CL Yu DR Boyd ND Sharma DT Gibson 2000 Regioselectivity and enantioselectivity of naphthalene dioxygenase during arene cis-dihydroxylation: control by phenylalanine 352 in the alpha subunit J Bacteriol 182 5495 5504
24. B Przybojewska 1999 Assessment of aniline derivatives-induced DNA damage in the liver cells of B6C3F1 mice using the alkaline single cell gel electrophoresis ('comet') assay Cancer Lett 147 1 4
25. JL Radomski 1979 The primary aromatic amines: their biological properties and structure-activity relationships Annu Rev Pharmacol Toxicol 19 129 157
26. HS Rai MS Bhattacharyya J Singh TK Bansal P Vats UC Banerjee 2005 Removal of dyes from the effluent of textile and dyestuff manufacturing industry: a review of emerging techniques with reference to biological treatment Crit Rev Environ Sci Technol 35 219 238
27. T Sakamoto JM Joern A Arisawa FH Arnold 2001 Laboratory evolution of toluene dioxygenase to accept 4-picoline as a substrate Appl Environ Microbiol 67 3882 3887
28. M Seeger M Zielinski KN Timmis B Hofer 1999 Regiospecificity of dioxygenation of di- to pentachlorobiphenyls and their degradation to chlorobenzoates by the bph-encoded catabolic pathway of Burkholderia sp. strain LB400 Appl Environ Microbiol 65 3614 3621
29. S Shardonofsky K Krishnan 1997 Characterization of methemoglobinemia induced by 3,5-xylidine in rats J Toxicol Environ Health 50 595 604
30. M Takeo T Fujii Y Maeda 1998 Sequence analysis of the genes encoding a multicomponent dioxygenase involved in oxidation of aniline and o-toluidine in Acinetobacter sp. strain YAA J Ferment Bioeng 85 17 24
31. M Takeo T Fujii K Takenaka Y Maeda 1998 Cloning and sequencing of a gene cluster for the meta-cleavage pathway of aniline degradation in Acinetobacter sp. strain YAA J Ferment Bioeng 85 514 517
32. M Urata E Uchida H Nojiri T Omori R Obo N Miyaura N Ouchiyama 2004 Genes involved in aniline degradation by Delftia acidovorans strain 7N and its distribution in the natural environment Biosci Biotechnol Biochem 68 2457 2465
33. LP Wackett 2002 Mechanism and applications of Rieske non-heme iron dioxygenases Enzyme Microbial Technol 31 577 587
34. EK Weisburger AB Russfield F Homburger JH Weisburger E Boger CGV Dongen KC Chu 1978 Testing of twenty-one environmental aromatic amines or derivatives for long-term toxicity or carcinogenicity J Environ Pathol Toxicol 2 325 356
35. HM Zhao 2007 Directed evolution of novel protein functions Biotechnol Bioeng 98 313 317
36. M Zielinski S Kahl C Standfuss-Gabisch B Camara M Seeger B Hofer 2006 Generation of novel-substrate-accepting biphenyl dioxygenases through segmental random mutagenesis and identification of residues involved in enzyme specificity Appl Environ Microbiol 72 2191 2199