Nitrile hydrolases

Industrial Enzymes: Structure, Function and Applications

Volumn , Issue , 2007, Pages 531-547

  Kaul, Praveen ^a   Banerjee, Anirban ^a   Banerjee, Uttam Chand ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84872153778     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/1-4020-5377-0_30     Document Type: Chapter

References (77)

1. Almatawah Q.A., Cramp R. and Cowan D.A. (1999). Characterization of an inducible nitrilase from a thermophilic Bacillus. Extremophiles 3, 283-291.
2. Banerjee A., Sharma R. and Banerjee U.C. (2002). Nitrile degrading enzymes: current status and future prospects. Appl. Microbiol. Biotechnol. 60, 33-44.
3. Banerjee A., Sharma R. and Banerjee U.C. (2003a). A rapid and sensitive fluorometric assay method for the determination of nitrilase activity. Biotechnol. Appl. Biochem. 37, 289-293.
4. Banerjee A., Kaul P., Sharma R. and Banerjee U.C. (2003b). A rapid colorimetric assay for enantioselective screening of nitrilase producing micro-organisms using pH sensitive indicators. J. Biomol. Screen. 8, 269-275.
5. Bartel B. and Fink G.R. (1994). Differential regulation of an auxin producing nitrilase gene family in Arabidopsis thaliana. Proc. Natl. Acad. Sci. USA 91, 6649-6653.
6. Bartling D., Seedorf M., Mithofer A. and Weiler E.W. (1992). Cloning and expression of an Arabidopsis nitrilase which can convert indole 3-acetonitrile to the plant hormone indole 3-acetic acid. Eur. J. Biochem. 205, 417-424.
7. Baumann M., Hauer B.H. and Bornscheuer U.T. (2000). Rapid screening of hydrolases for the enantioselective conversion of difficult to resolve substrates. Tetrahedron: Asymmetry 11, 4781-4790.
8. Bestwick L.A., Gronning L.M., James D.C., Bones A. and Rossiter J.T. (1993). Purification and characterization of a nitrilase from Brassica nupus. Physiol. Plant 89, 811-816.
9. Bhalla T.C., Miura A., Wakamoto A., Ohba Y. and 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.
10. Brenner C. (2002). Catalysis in the nitrilase superfamily. Curr. Opin. Strc. Biol. 12, 775-782.
11. Cawston T. (1996). Metalloproteinase inhibitors and the prevention of connective tissue breakdown. Pharmacol. Ther. 70, 163-182.
12. Chassin C. (1996). A biotechnological process for the production of nicotinamide. Chim. Oggi 14, 9-12.
13. Chebrou H., Bigey F., Arnaud A. and Glazy P. (1996). Study of the amidase signature group. Biochem. Biophys. Acta. 1298, 285-293.
14. Dadd M.R., Sharp D.C.A., Pettman A.J. and Knowles C.J. (2000). Real-time monitoring of nitrile biotransformations by mid-infrared spectroscopy. J. Microb. Meth. 41, 69-75.
15. DiCosimo R., Fallon R.D., Gavagan J.E. and Herkes F.E. (2000) US Patent 6066490, to E.I. DuPont, USA.
16. Endo T. and Tamura K. (1993) US Patent 5223416, to Nitto Chemical Industry Co. Ltd., Japan.
17. Endo I., Okada M. and Yohda M. (1999). An enzyme controlled by light: the molecular mechanism of photoreactivity in nitrile hydratase. Trends in Biotechnol. 17, 244-248.
18. Faber K. (1997) Biotransformation in organic chemistry: A textbook. Berlin: Springer.
19. Fawcett J.K. and Scott J.E. (1960). A rapid and precise method for the determination of urea. J. Clin. Pathol. 13, 156-159.
20. Fournand D., Bigey F. and 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.
21. Freyssinet G., Peleissier B., Fressinet M. and Delon R. (1996). Crops resistant to oxynils: From laboratory to market. Field Crops Res. 45, 125-133.
22. Gao W., Mitsuya H., Driscoll J. and Johns D. (1995). Enhancement by hydroxyurea of the antihuman immunodefficiency virus type 1 potency of 2'- β-fluoro-2', 3'dideoxyadenosine in peripheral blood mononuclear cells. Biochem. Pharmacol. 50, 274-276.
23. Gibbons B.H. and Edsall J.T. (1963). Rate of hydration of carbon dioxide and dehydration of carbonic anhydrase at 25 °C. J. Biol. Chem. 238, 3502-3507.
24. Godtfredsen S.E., Ingvorsen K., Yde B. and Anderson O. (1985). Biocatalysis in organic synthesis. Amsterdam: Elsevier.
25. Goldhust A. and Bohak Z. (1989). Induction, purification and characterization of the nitrilase of Fusarium oxysporum. Biotechnol. Appl. Biochem. 11, 581-601.
26. Harper D.B. (1977). Fungal degradation of aromatic nitriles: Enzymology of C-N cleavage by Fusarium solani. Biochem. J. 167, 685-692.
27. Hashimoto Y., Kobayashi E., Endo T., Nishiyama M. and Horinouchi S. (1996). Conversion of a cyanohydrin compound into S-(-)-3-phenyllactic acid by enantioselective hydrolytic activity of Pseudomonas sp. BC-18. Biosci. Biotech. Biochem. 60, 1273-1283.
28. Hillebrand H., Bartling D. and Weiler E.W. (1998). Structural analysis of the nit2/nit1/nit3 gene cluster encoding nitrilases, enzymes catalyzing the terminal activation step in indole 3-acetic acid biosynthesis in Arabidopsis thaliana. Plant Mol. Biol. 36, 89-99.
29. Hook R.H. and Robinson W.G. (1964). Ricinine nitrilase II. Purification and properties. J. Biol. Chem. 239, 4263-4267.
30. Huang W., Jia J., Cummings J., Nelson M., Schneder G. and Lindqvist Y. (1997). Crystal structure of nitrile hydratase reveals a novel iron centre in a novel fold.rystal structure of nitrile hydratase reveals a novel iron centre in a novel fold. Structure 5, 691-699.
31. Kato Y., Nakamura K., Sakiyama H., Mathew S.G. and Asano Y. (2000). Novel heme-containing lyase, phenylacetaldoxime dehydratase from Bacillus Sp. strain OxB-1: Purification, characterization and molecular cloning of the gene. Biochemistry 39, 800-809.
32. Kaul P., Banerjee A. and Banerjee U. (2004a). Biocatalysis: Applications and potential for the pharmaceutical industry. Drug Discov. World Spring Issue: 80-86.
33. Kaul P., Banerjee A., Mayilraj S. and Banerjee U.C. (2004b). Screening for enantioselective nitrilases: kinetic resolution of racemic mandelonitrile to R-mandelic acid by new bacterial isolates. Tetrahedron: Asymmetry 15, 207-211.
34. Khachadurian A., Knox W.E. and Cullen A.M. (1960). Colorimetric ninhydrin method for total alpha amino acids of urine. J. Lab. Clin. Med. 56, 321-325.
35. Kobayashi K., Yanaka N., Nagasawa T. and Yamada H. (1992). Primary structure of an aliphatic nitrilase from Rhodococcus rhodochrous K22 and expression of its gene and identification of its active site residue. Biochemistry 31, 9000-9007.
36. Kobayashi M., Izui H., Nagasawa T. and Yamada H. (1993). Nitrilase in biosynthesis of the plant hormone indole-3-acetic acid from indole-3- acetonitrile: Cloning of the Alcaligenes gene and site directed mutagenesis of cysteine residues. Proc. Natl. Acad. Sci. USA 90, 247-251.
37. Kobayashi M. and Shimizu S. (1994). Versatile nitrilases: Nitrile-hydrolysing enzymes. FEMS Microbiol. Lett. 120, 217-224.
38. Kobayashi M., Goda M. and Shimizu S. (1998). Nitrilase catalyzes amide hydrolysis as well as nitrile hydrolysis. Biochem. Biophys. Res. Comm. 253, 662-666.
39. Komeda H., Hori Y., Kobayashi M. and Shimizu S. (1996a). Transcriptional regulation of the Rhodococcus rhodochrous J1 nitA gene encoding a nitrilase. Proc. Natl. Acad. Sci. USA 93, 10572-10577.
40. Komeda H., Kobayashi M. and Shimizu S. (1996b). A novel gene cluster including the R. rhodochrous J1 nhi BA genes encoding a new low molecular mass nitrile hydratase (L-NHase) induced by it's reaction product. J. Biol. Chem. 271, 15796-15802.
41. Krallmann-Wenzel U. (1985). An improved method of ammonia determination, applicable to amidases and other ammonia producing enzyme systems of mycobacteria. Am. Rev. Respir. Dis. 131, 432-434.
42. Kruse J.M. and Mellon M.J. (1953). Colorimetric determination of ammonia and cyanate. Anal. Chem. 25, 1188-1192.
43. Layh N., Parratt J. and Willetts A. (1998). Characterization and partial purification of an enantioselective arylacetonitrilase from Pseudomonas fluorescens DSM 7155. J. Mol. Cat. B: Enz. 5, 467-474.
44. Lebuhn M. and Hartmann A. (1993). Method for the determination of indole-3-acetic acid and related compounds of L-tryptophan catabolism in soils. J. Chromat. A 629, 255-266.
45. Lowry O.H., Roberts N.R., Wu M.L., Hixon W.S. and Crawford E.J. (1954). The quantitave histochemistry of brain II - Enzymatic measurements. J. Biol. Chem. 207, 19-37.
46. Martin R.G. and Rosner J.L. (2001). The AraC transcrptional activators. Curr. Opin. Microbiol. 4, 132-137.
47. McBride K.E., Kenny J.W. and Stalker D.M. (1986). Metabolism of the herbicide bromoxynil by Klebsiella pneumomiae subsp. ozanae. Appl. Environ. Microbiol. 52, 325-330.
48. Muller D. and Gabriel J. (1999). Bacterial degradation of the herbicide bromoxynil by Agrobacterium radiobacter in biofilm. Folia Mikrobiologia 44, 377-379.
49. Nagasawa T., Takeuchi K., Nardi-Devi V., Mihara Y. and Yamada H. (1991). Optimum culture conditions for the production of cobalt containing nitrile hydratase by Rhodococcus rhodochrous J1. Appl. Microbiol. Biotechnol 34, 783-788.
50. Nagasawa T. (1993). The superiority of the third generation catalyst, Rhodococcus rhodochrous J1 nitrile hydratase, for industrial production of acrylamide. Appl. Microbiol. Biotechnol. 40, 189-195.
51. Nagasawa T., Wieser M., Nakamura T., Iwahara H., Yoshida T. and Gekko K. (2000). Nitrilase of Rhodococcus rhodochrous J1, conversion into the active form by subunit association. Eur. J. Biochem. 267, 138-144.
52. Nakai T., Hasegawa T., Yamashita E., Yamamoto M., Kumaska T., Ueki T., Nanba H., Ikenaka Y., Sato M. and Tsukihara T. (2000). Crystal structue of N-carbamyl-D-amino acid amidohydrolase with a novel catalytic framework common to amido hydrolases. Structure 8, 729-739.
53. Nawaz M., Khan A., Bhattacharya D., Sittoneu P. and Cerniglia C. (1996). Physical, biochemical, and immunological characterization of a thermostable amidase from Klebsiella pneumoniae NCTR 1. J. Bacteriol. 178, 2397-2401.
54. Nishise H., Kurihara M. and Tani Y. (1987). Microbial synthesis of tranexamic acid intermediate from dinitrile. Agric. Biol. Chem. 51, 2613-2616.
55. O'Reilly C. and Turner P.D. (2003). The nitrilase family of CN hydrolysing enzymes - a comparative study. J. Appl. Microbiol. 95, 1161-1174.
56. Pace H.C. and Brenner C. (2001). The nitrilase superfamily: Classification, structure and function. Genome Biol. 2, 1-9.
57. Patel R.N. (2001). Biocatalytic synthesis of intermediates for the synthesis of chiral drug substances. Curr. Opin. Biotechnol. 12, 587-604.
58. Payne M., Wu S., Fallon R., Tudor G., Turner I., Steglitz B. and Nelson M. (1997). A stereoselective cobalt containing nitrile hydratase. Biochemistry 36, 5447-5454.
59. Piotrowski M., Schonfelder S. and Weiler E.W. (2001). The Arabidopsis thaliana isogene NIT4 and its orthologs in tobacco encode beta cyano L-alanine hydratase/nitrilase. J. Biol. Chem. 276, 2616-2621.
60. Pollak P., Romender G., Hagedorn F. and Gelbke H.P. (1991) Ullmans encyclopaedia of industrial chemistry. Weinheim: Wiley - VCH.
61. Ress-Loschke M., Friedrich T., Hauer B., Mattes R. and Engels D. (1998) DE198448129A1, to BASF.
62. Schill S. Levy, Soubrier F., Coq A.M.C.-L., Faucher D., Crouzet J. and Petre D. (1995). Aliphatic nitrilase from a soil isolated Comamonas testoteroni sp. gene cloning and overexpression, purification and primary structure. Gene 161, 15-20.
63. Schmid A., Dordick J.S., Hauer B., Kiener A., Wubbolts M. and Witholt B. (2001). Industrial biocatalysis today and tomorrow. Nature 409, 258-268.
64. Simons S.S. and Johnson D.F. (1976). The structure of the fluorescent adduct formed in the reaction of o-phthalaldehyde and thiols with amines. J. Am. Chem. Soc. 98, 7098-7099.
65. Simons S.S. and Johnson D.F. (1978). Reaction of o-phthalaldehyde and thiols with primary amines: formation of 1-alkyl(and aryl)thio-2- alkylisoindoles. J. Org. Chem. 43, 2886-2891.
66. Solomonson L.P. and Spehar A.M. (1981) Cyanide as a metabolic inhibitor. London: Academic Press.
67. Stalker D.M., Mcbride K.E. and Malyj L.D. (1988). Herbicide resistence in transgenic plants expressing a bacterial detoxification gene. Science 242, 419-423
68. Sugai T., Yamazaki T., Yokoyama M. and Ohta H. (1997). Biocatalysis in organic synthesis: The use of nitrile and amide-hydrolyzing micro-organisms. Biosci. Biotech. Biochem. 61, 1419-1427.
69. Sugiura Y., Kuwahara J., Nagasawa T. and Yamada H. (1987). Nitrile hydratase: the first non-heme iron enzyme with a typical low spin Fe(III) active centre. J. Am. Chem. Soc. 109, 5848-5850.
70. Thimann K.V. and Mahadevan S. (1964). Nitrilase, its substrate specificity and possible mode of action. Arch. Biochem. Biophys. 107, 62-68.
71. Tsunoda H. and Yamaguchi K. (1995). The cDNA sequence of an auxin producing nitrilase homologue in tobacco. Plant Physiol. 109, 339.
72. Wu Z.L. and Li Z.Y. (2003). Biocatalytic asymmetric hydrolysis of (±)-beta hydroxy nitriles by Rhodococcus sp. CGMCC 0497. J. Mol. Cat. B: Enz. 22, 105-112.
73. Wyatt J.M. and Knowles C.J. (1995). Microbial degradation of acrylonitrile waste effluents: the degradation of effluents and and codendsates from the manufacture of acrylonitrile. Int. Biodeter. Biodegrad. 227-248.
74. Yamada H. and Nagasawa T. (1994) US Patent 5334519, to Nitto Chemical Industry Co. Ltd. Japan.
75. Yamada H. and Kobayashi M. (1996). Nitrile hydratase and it's application to industrial production of acrylamide. Biosci. Biotech. Biochem. 60, 1391-1400.
76. Yamamoto K., Ueno Y., Otsubo K., Kawakami K. and Komatsu K. (1990). Production of (S)-(+)-ibuprofen from a nitrile compound by Acinetobacter sp. AK 226. Appl. Environ. Microbiol. 56, 3125-3129.
77. Yamamoto K., Ueno Y., Otsubo K., Yamane H., Komatsu K. and Tani Y. (1992). Efficient conversion of dinitrile to mononitrile -monocarboxylic acid by Corynebacterium sp. C5 cells during tranexamic acid synthesis. J. Ferment. Bioeng. 73, 125-129.