Multiple mutations at the active site of naphthalene dioxygenase affect regioselectivity and enantioselectivity

Journal of Industrial Microbiology and Biotechnology

Volumn 27, Issue 2, 2001, Pages 94-103

  Yu, C L ^a   Parales, R E ^a   Gibson, D T ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

Aromatic hydrocarbons; Biodegradation; Dioxygenase; Naphthalene; Site directed mutagenesis

Indexed keywords

2 NITROTOLUENE; 2-NITROTOLUENE; AROMATIC HYDROCARBON; BIPHENYL; BIPHENYL DERIVATIVE; DRUG DERIVATIVE; INDOLE; INDOLE DERIVATIVE; INDOLINE; MULTIENZYME COMPLEX; NAPHTHALENE; NAPHTHALENE DERIVATIVE; NAPHTHALENE DIOXYGENASE; OXYGENASE; PHENANTHRENE; PHENANTHRENE DERIVATIVE; TOLUENE;

ARTICLE; BINDING SITE; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; METABOLISM; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTEIN CONFORMATION; PSEUDOMONAS; SITE DIRECTED MUTAGENESIS; STEREOISOMERISM; WESTERN BLOTTING;

BINDING SITES; BIPHENYL COMPOUNDS; BLOTTING, WESTERN; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ESCHERICHIA COLI; HYDROCARBONS, AROMATIC; INDOLES; MULTIENZYME COMPLEXES; MUTAGENESIS, SITE-DIRECTED; NAPHTHALENES; OXYGENASES; PHENANTHRENES; PROTEIN CONFORMATION; PSEUDOMONAS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TOLUENE;

EID: 0035434478     PISSN: 13675435     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.jim.7000168     Document Type: Article

References (45)

1. An D. DT Gibson and JC Spain. 1994. Oxidative release of nitrite from 2-nitrotoluene by a three-component enzyme system from Pseudomonas sp. strain JS42. J Bacteriol 176: 7462-7467.
2. Ausubel FM, R Brent, RE Kingston, DD Moore, JG Seidman, JA Smith and K Struhl. 1993. Current Protocols in Molecular Biology. Wiley, New York.
3. Beil S, B Happe, KN Timmis and DH Pieper. 1997. Genetic and biochemical characterization of the broad spectrum chlorobenzene dioxygenase from Burkholderia sp. strain PS12 - dechlorination of 1,2,4,5-tetrachlorobenzene. Eur J Biochem 247: 190-199.
4. Beil S, JR Mason, KN Timmis and DH Pieper. 1998. Identification of chlorobenzene dioxygenase sequence elements involved in dechlorination of 1.2,4,5-tetrachlorobenzene. J Bacteriol 180: 5520-5528.
5. Carredano E. 1999. PhD Thesis. Swedish University of Agricultural Sciences, Uppsala, Sweden.
6. Carredano E, A Karlsson, B Kauppi, D Choudhury, RE Parales, JV Parales, K Lee, DT Gibson, H Eklund and S Ramaswamy. 2000. Substrate binding site of naphthalene 1,2-dioxygenase: functional implications of indole binding. J Mol Biol 296: 701-712.
7. Davis RW, D Botstein and JR Roth. 1980. Advanced Bacterial Genetics. Cold Spring Harbor Laboratory. Cold Spring Harbor, NY.
8. Ensley BD and DT Gibson. 1983. Naphthalene dioxygenase: purification and properties of a terminal oxygenase component. J Bacteriol 155: 505-511.
9. 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.
10. 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.
11. Gibson DT and RE Parales. 2000. Aromatic hydrocarbon dioxygenases in environmental biotechnology. Curr Opin Biotechnol 11: 236-243.
12. Gibson DT, RL Roberts, MC Wells and VM Kobal. 1973. Oxidation of biphenyl by a Beijerinckia species. Biochem Biophys Res Commun 50: 211-219.
13. 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.
14. Guengerich FP. 1991. Reactions and significance of cytochrome P-450 enzymes. J Biol Chem 266: 10019-10022.
15. NAp, a component of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816. J Bacteriol 172: 465-468.
16. NAP reductase. a component of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816. J Bacteriol 172: 457-464.
17. Haigler BE, WH Wallace and JC Spain. 1994. Biodegradation of 2-nitrotoluene by Pseudomonas sp. strain JS42. Appl Environ Microbiol 60: 3466-3469.
18. Harlow E and D Lane. 1988. Antibodies, A Laboratory Manual. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY.
19. Hudlicky T, D Gonzalez and DT Gibson. 1999. Enzymatic dihydroxylation of aromatics in enantioselective synthesis: expanding asymmetric methodology. Aldrichimica Acta 32: 35-62.
20. Jeffrey AM, HJC Yeh, DM Jerina, TR Patel, JF Davey and DT Gibson. 1975. Initial reactions in the oxidation of naphthalene by Pseudomonas putida. Biochemistry 14: 575-583.
21. 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.
22. 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.
23. Kauppi B, K Lee, E Carredano, RE Parales, DT Gibson, H Eklund and S Ramaswamy. 1998. Structure of an aromatic ring-hydroxylating dioxygenase - naphthalene 1,2-dioxygenase. Structure 6: 571-586.
24. Lee S - Y and S Rasheed. 1990. A simple procedure for maximum yield of high - quality plasmid DNA. BioTechniques 9: 676-679.
25. Lynch NA, H Jiang and DT Gibson. 1996. Rapid purification of the oxygenase component of toluene dioxygenase from a polyol-responsive monoclonal antibody. Appl Environ Microbiol 62: 2133-2137.
26. 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 181: 57-61.
27. Parales JV, RE Parales, SM Resnick and DT Gibson. 1998. Enzyme specificity of 2-nitrotoluene 2,3-dioxygenase from Pseudomonas sp. strain JS42 is determined by the C - terminal region of the a subunit of the oxygenase component. J Bacteriol 180: 1194-1199.
28. Parales RE, MD Emig, NA Lynch and DT Gibson. 1998. Substrate specificities of hybrid naphthalene and 2,4-dinitrotoluene dioxygenase enzyme systems. J Bacteriol 180: 2337-2344.
29. Parales RE, JV Parales and DT Gibson. 1999. Aspartate 205 in the catalytic domain of naphthalene dioxygenase is essential for activity. J Bacteriol 181: 1831-1837.
30. Parales RE, K Lee, SM Resnick, H Jiang, DJ Lessner and DT Gibson. 2000. Substrate specificity of naphthalene dioxygenase: effect of specific amino acids at the active site of the enzyme. J Bacteriol 182: 1641-1649.
31. Parales RE, SM Resnick, CL Yu, DR Boyd, ND Sharma and DT Gibson. 2000. Regioselectivity and enantioselectivity of naphthalene dioxygenase during arene cis-dihydroxylation: control by phenylalanine 352 in the a subunit. J Bacteriol 182: 5495-5504.
32. Resnick S. 1997. PhD Thesis. University of Iowa, Iowa City, IA.
33. 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.
34. 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.
35. 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.
36. Resnick SM, K Lee and DT Gibson. 1996. Diverse reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816. J Ind Microbiol 17: 438-457.
37. Sambrook J, EF Fritch and T Maniatis. 1989. Molecular Cloning: A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY.
38. 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.
39. Stanier RY, NJ Palleroni and M Doudoroff. 1966. The aerobic pseudomonads; a taxonomic study. J Gun Microbiol 43: 159-271.
40. Suen W-C. 1991. PhD Thesis. University of Iowa, Iowa City, IA.
41. Suen W-C, BE Haigler and JC Spain. 1996. 2,4-Dinitrotoluene dioxygenase from Burkholderia sp. strain DNT: similarity to naphthalene dioxygenase. J Bacteriol 178: 4926-4934.
42. Tabor S and CC Richardson. 1985. A bacteriophage T7 RNA polymerase/promoter system for controlled exclusive expression of specific genes. Proc Natl Acad Sci USA 82: 1074-1078.
43. Werlen C, H-P Kohler and JR van der Meer. 1996. The broad substrate chlorobenzene dioxygenase and cis-chlorobenzene dihydrodiol dehydrogenase of Pseudomonas sp. strain P51 are linked evolutionarily to the enzymes for benzene and toluene degradation. J Biol Chem 271: 4009-4016.
44. Yanisch-Perron C. J Vieira and J Messing. 1985. Improved M13 phage cloning vectors and host strains: nucleotide sequences of the M13mp18 and pUC19 vectors. Gene 33: 103-119.
45. Zylstra GJ and DT Gibson. 1989. Toluene degradation by Pseudomonas putida F1: nucleotide sequence of the todC/C2BADE genes and their expression in E. coli. J Biol Chem 264: 14940-14946.