Biotransformation of benzonitrile herbicides via the nitrile hydratase-amidase pathway in rhodococci

Journal of Industrial Microbiology and Biotechnology

Volumn 39, Issue 12, 2012, Pages 1811-1819

  Veselá, Alicja B ^a   Pelantová, Helena ^a   Šulc, Miroslav ^b   MacKová, Martina ^c   Lovecká, Petra ^c   Thimová, Markéta ^c   Pasquarelli, Fabrizia ^d   Pičmanová, Martina ^a   Pátek, Miroslav ^a   Chand Bhalla, Tek ^e   Martínková, Ludmila ^a  

^a INSTITUTE OF MATHEMATICS   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

^c INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^d UNIVERSITY OF L'AQUILA   (Italy)

^e HIMACHAL PRADESH UNIVERSITY   (India)

Author keywords

Amidase; Benzonitrile herbicides; Nitrile hydratase; Rhodococcus erythropolis; Rhodococcus rhodochrous

Indexed keywords

2,6 DICHLOROBENZAMIDE; 2,6 DICHLOROBENZOIC ACID; 3,5 DICHLORO 4 HYDROXYBENZONITRILE; 3,5 DIIODO 4 HYDROXYBENZONITRILE; AMIDASE; AMIDE; BENZONITRILE; BROMOXYNIL; CARBOXYLIC ACID; HERBICIDE; NITRILE HYDRATASE; UNCLASSIFIED DRUG;

ARTICLE; DETOXIFICATION; FUNGAL STRAIN; HYDROLYSIS; LACTUCA; MINERALIZATION; NONHUMAN; PLANT GROWTH; PLANT ROOT; RHODOCOCCUS; TOXICITY;

AMIDES; AMIDOHYDROLASES; BENZAMIDES; BIOTRANSFORMATION; HERBICIDES; HYDRO-LYASES; HYDROLYSIS; IODOBENZENES; LETTUCE; NITRILES; PLANT ROOTS; RHODOCOCCUS;

LACTUCA SATIVA; RHODOCOCCUS ERYTHROPOLIS; RHODOCOCCUS RHODOCHROUS;

EID: 84872158771     PISSN: 13675435     EISSN: 14765535     Source Type: Journal    
DOI: 10.1007/s10295-012-1184-z     Document Type: Article

References (37)

1. Avaniss-Aghajani E, Jones K, Holtzman A, Aronson T, Glover N, Boian M, Froman S, Brunk CF (1996) Molecular technique for rapid identification of mycobacteria. J Clin Microbiol 34:98-102
2. Bhalla TC, Aoshima M, Misawa S, Muramatsu R, Furuhashi K (1995) The molecular cloning and sequencing of the nitrilase gene of Rhodococcus rhodochrous PA-34. Acta Biotechnol 15:297-306
3. Bhalla TC, Miura A, Wakamoto A, Ohba Y, Furuhashi K (1992) Asymmetric hydrolysis of alpha aminonitriles to optically active amino acids by a nitrilase of Rhodococcus rhodochrous PA-34. Appl Microbiol Biotechnol 37:184-190
4. Brandao PFB, Clapp JP, Bull AT (2003) Diversity of nitrile hydratase and amidase enzyme genes in Rhodococcus erythropolis recovered from geographically distinct habitats. Appl Environ Microbiol 69:5754-5766
5. DiGeronimo MJ, Antoine AD (1976) Metabolism of acetonitrile and propionitrile by Nocardia rhodochrous LL100-21. Appl Environ Microbiol 31:900-906
6. Fournand D, Bigey F, Arnaud A (1998) Acyl transfer activity of an amidase from Rhodococcus sp. strain R312: formation of a wide range of hydroxamic acids. Appl Environ Microbiol 64:2844-2852
7. Freyssinet G, Pelissier B, Freyssinet M, Delon R (1996) Crops resistant to oxynils: from the laboratory to the market. Field Crops Res 45:125-133
8. Harper DB (1985) Characterization of a nitrilase from Nocardia sp. (rhodochrous group) N.C.I.B. 11215, using p-hydroxybenzonitrile as sole carbon source. Int J Biochem 17:677-683
9. Holtze MS, Sørensen J, Hansen HCB, Aamand J (2006) Transformation of the herbicide 2,6-dichlorobenzonitrile to the persistent metabolite 2,6-dichlorobenzamide (BAM) by soil bacteria known to harbour nitrile hydratase or nitrilase. Biodegradation 17:503-510
10. Holtze MS, Sørensen SR, Sørensen J, Aamand J (2008) Microbial degradation of the benzonitrile herbicides dichlobenil, bromoxynil and ioxynil in soil and subsurface environments - Insights into degradation pathways, persistent metabolites and involved degrader organism. Environ Pollut 154:155-168
11. Komeda H, Kobayashi M, Shimizu S (1996) A novel gene cluster including the Rhodococcus rhodochrous J1 nhlBA genes encoding a low molecular mass nitrile hydratase (L-NHase) induced by its reaction product. J Biol Chem 271:15796-15802
12. Komeda H, Kobayashi M, Shimizu S (1996) Characterization of the gene cluster of high-molecular-mass nitrile hydratase (HNHase) induced by its reaction product in Rhodococcus rhodochrous J1. Proc Natl Acad Sci USA 93:4267-4272
13. Kubáč D, Kaplan O, Elišáková V, Pátek M, Vejvoda V, Slámová K, Tóthová A, Lemaire M, Gallienne E, Lutz-Wahl S, Fischer L, Kuzma M, Pelantová H, van Pelt S, Bolte J, Křen V, Martínková L (2008) Biotransformation of nitriles to amides using soluble and immobilized nitrile hydratase from Rhodococcus erythropolis A4. J Mol Catal B Enzym 50:107-113
14. Martínková L, Uhnáková B, Pátek M, Nešvera J, Křen V (2009) Biodegradation potential of the genus Rhodococcus. Environ Int 35:162-177
15. McBride KE, Kenny JW, Stalker DM (1986) Metabolism of the herbicide bromoxynil by Klebsiella pneumoniae. Appl Environ Microbiol 52:325-330
16. Meth-Cohn O, Wang MX (1997) An in-depth study of the biotransformation of nitriles into amides and/or acids using Rhodococcus rhodochrous AJ270. J Chem Soc Perkin Trans I:1099-1104
17. Nielsen MKK, Holtze MS, Svensmark B, Juhler RK (2007) Demonstrating formation of potentially persistent transformation products from the herbicides bromoxynil and ioxynil using liquid chromatography-tandem mass spectrometry (LC-MS/MS) . Pestic Manag Sci 63:141-149
18. Pace HC, Brenner C (2001) The nitrilase superfamily: classification, structure and function. Genome Biol 2:0001.1-0001.9
19. Prasad S, Raj J, Bhalla TC (2009) Purification of a hyperactive nitrile hydratase from resting cells of Rhodococcus rhodochrous PA-34. Ind J Microbiol 49:237-242
20. Raj J, Prasad S, Bhalla TC (2006) Rhodococcus rhodochrous PA- 34: a potential biocatalyst for acrylamide synthesis. Process Biochem 41:1359-1363
21. Raj J, Seth A, Prasad S, Bhalla TC (2007) Bioconversion of butyronitrile to butyramide using whole cells of Rhodococcus rhodochrous PA-34. Appl Microbiol Biotechnol 74:535-539
22. Rosenbrock P, Munch JC, Scheunert I, Do?rfler U (2004) Biodegradation of the herbicide bromoxynil and its plant cell wall bound residues in an agricultural soil. Pestic Biochem Physiol 78:49-57
23. Simonsen A, Holtze MS, Sørensen SR, Aamand J (2006) Mineralisation of 2,6-dichlorobenzamide (BAM) in dichlobenilexposed soils and isolation of a BAM-mineralising Aminobacter sp. Environ Pollut 144:289-295
24. Sjøholm OR, Aamand J, Sørensen SR, Nybroe O (2010) Degrader density determines spatial variability of 2,6-dichlorobenzamide mineralization in soil. Environ Pollut 158:292-298
25. Sjøholm OR, Nybroe O, Aamand J, Sørensen SR (2010) 2,6- Dichlorobenzamide (BAM) herbicide mineralisation by Aminobacter sp. MSH1 during starvation depends on a subpopulation of intact cells maintaining vital membrane functions. Environ Pollut 158:3618-3625
26. Smith AE, Cullimore DR (1974) The in vitro degradation of herbicide bromoxynil. Can J Microbiol 20:773-776
27. Song L, Wang M, Shi J, Xue Z, Wang MX, Qian S (2007) High resolution X-ray molecular structure of the nitrile hydratase from Rhodococcus erythropolis AJ270 reveals posttranslational oxidation of two cysteines into sulfinic acids and a novel biocatalytic nitrile hydration mechanism. Biochem Biophys Res Commun 362:319-324
28. Sørensen SR, Holtze MS, Simonsen A, Aamand J (2007) Degradation and mineralization of nanomolar concentrations of the herbicide dichlobenil and its persistent metabolite 2,6-dichlorobenzamide by Aminobacter spp. isolated from dichlobenil-treated soils. Appl Environ Microbiol 73:399-406
29. Stalker DM, Malyj LD, McBride KE (1988) Purification and properties of a nitrilase specific for the herbicide bromoxynil and corresponding nucleotide sequence analysis of the bxn gene. J Biol Chem 263:6310-6314
30. Turner S, Pryer KM, Miao VP, Palmer JD (1999) Investigating deep phylogenetic relationships among cyanobacteria and plastids by small subunit rRNA sequence analysis. J Eukaryot Microbiol 46:327-338
31. Veková J, Pavlu L, Vosáhlo J, Gabriel J (1995) Degradation of bromoxynil by resting and immobilized cells of Agrobacterium radiobacter 8/4-strain. Biotechnol Lett 17:449-452
32. Veselá AB, Franc M, Pelantová H, Kubáč D, Vejvoda V, Šulc M, Bhalla TC, Macková M, Lovecká P, Janu P, Demnerová K, Martínková L (2010) Hydrolysis of benzonitrile herbicides by soil actinobacteria and metabolite toxicity. Biodegradation 21:761
33. Veselá AB, Franc M, Pelantová H, Kubáč D, Vejvoda V, Šulc M, Bhalla TC, Macková M, Lovecká P, Janu P, Demnerová K, Martínková L (2010) Hydrolysis of benzonitrile herbicides by soil actinobacteria and metabolite toxicity. Biodegradation 22:1255
34. Vokounová M, Vacek O, Kunc F (1992) Degradation of the herbicide bromoxynil in Pseudomonas putida. Folia Microbiol 37:122-127
35. Vosáhlová J, Pavlu L, Vosáhlo J, Brenner V (1997) Degradation of bromoxynil, ioxynil, dichlobenil and their mixtures by Agrobacterium radiobacter 8/4. Pestic Sci 49:303-306
36. Wieser M, Takeuchi K, Wada Y, Yamada H, Nagasawa T (1998) Low-molecular-mass nitrile hydratase from Rhodococcus rhodochrous J1: purification, substrate specificity and comparison with the analogous high-molecular-mass enzyme. FEMS Microbiol Lett 169:17-22
37. Xie SX, Kato Y, Komeda H, Yoshida S, Asano Y (2003) A gene cluster responsible for alkylaldoxime metabolism coexisting with nitrile hydratase and amidase in Rhodococcus globerulus A-4. Biochemistry 42:12056-12066