Enantioselective hydration of a arylpropionitriles by a nitrile hydratase from Agrobacterium tumefaciens strain d3

Applied Microbiology and Biotechnology

Volumn 49, Issue 1, 1998, Pages 89-95

  Bauer, R ^a   Knackmuss, H J ^a   Stolz, A ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 ARYLPROPIONITRILE; NITRILE HYDRATASE; PROPIONITRILE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; ENANTIOMER; ENZYME ACTIVITY; HYDRATION; NONHUMAN; RHIZOBIUM RADIOBACTER; STEREOCHEMISTRY; TEMPERATURE;

AGROBACTERIUM TUMEFACIENS; BACTERIA (MICROORGANISMS);

EID: 0031963112     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002530051142     Document Type: Article

References (40)

1. Arcus CL, Kenyon J (1939) The mechanism of the Hofmann reaction. Retention of optical activity during the reaction with (+)hydratropamide. J Chem Soc 916-919
2. Asano Y, Fujishiro K, Tani Y, Yamada H (1982) Aliphatic nitrile hydratase from Arthrobacter sp. J-1. Purification and characterization. Agric Biol Chem 46: 1165-1174
3. Bauer R, Hirrlinger B, Layh N, Stolz A, Knackmuss H-J (1994) Enantioselective hydrolysis of racemic 2-phenylpropionitrile and other (R,S)-2-arylpropionitriles by a new bacterial isolate. Agrobacterium tumefaciens strain d3. Appl Microbiol Biotechnol 42: 1-7
4. Beard T, Cohen MA, Parratt JS, Turner NJ, Crosby J, Moilliet J (1993) Stereoselective hydrolysis of nitriles and amides under mild conditions using a whole cell catalyst. Tetrahedron Asymmetry 4: 1085-1104
5. Blakey AJ, Colby J, Williams E, O'Reilly C (1995) Regio- and stereo-specific nitrile hydrolysis by the nitrile hydratase from Rhodococcus AJ270. FEMS Microbiol Lett 129: 57-62
6. Cohen MA, Parratt JS, Turner NJ (1992) Enantioselective hydrolysis of nitriles and amides using an immobilised whole cell system. Tetrahedron Asymmetry 3: 1543-1546
7. Cram DJ, Haberfield P (1961) Electrophilic substitution at saturated carbon. XI. Steric course of the base-catalyzed decarboxylation reaction. J Am Chem Soc 83: 2354-2361
8. Duran R, Nishiyama M, Horinouchi S, Beppu T (1993) Characterization of nitrile hydratase genes cloned by screeing from Rhodococcus erythropolis. Biosci Biotechnol Biochem 57: 1323-1328
9. Faber K, Ottolina G, Riva S (1993) Selectivity-enhancement of hydrolase reactions. Biocatalysis 8: 91-132
10. Fallon RD, Stieglitz B, Turner I Jr (1997) A Pseudomonas putida capable of stereoselective hydrolysis of nitriles. Appl Microbiol Biotechnol 47: 156-161
11. Gradley ML, Knowles CJ (1994) Asymmetric hydrolysis of chiral nitriles by Rhodococcus rhodochrous NCIMB 11216 nitrilase. Biotechnol Lett 16: 41-46
12. Hirrlinger B, Stolz A, Knackmuss H-J (1996) Purification and properties of an amidase from Rhodococcus erythropolis MP50 which enantioselectively hydrolyzes 2-arylpropionamides. J Bacteriol 178: 3501-3507
13. Kakeya H, Sakai N, Sugai T, Ohta H (1991) Microbial hydrolysis as a potent method for the preparation of optically active nitriles, amides and carboxylic acids. Tetrahedron Lett 32: 1343-1346
14. Kobayashi M, Fujita T, Shimizu S (1996) Hyperinduction of nitrile hydratase acting on indole-3-acetonitrile in Agrobacterium tumefaciens. Appl Microbiol Biotechnol 45: 176-181
15. Kobayashi M, Shimizu S (1994) Versatile nitrilases: nitrile-hydrolysing enzymes. FEMS Microbiol Lett 120: 217-224
16. Kobayashi M, Komeda H, Nagasawa T, Nishiyama M, Horinouchi S, Beppu T, Yamada H, Shimizu S (1993) Amidase coupled with low-molecular-mass nitrile hydratase from Rhodococcus rhodochrous J1. Eur J Biochem 217: 327-336
17. Kobayashi M, Nagasawa T, Yamada H (1992) Enzymatic synthesis of acrylamide: a success story not yet over. Trends Biotechnol 10: 402-408
18. Kobayashi M, Suzuki T, Fujita T, Masuda M, Shimizu S (1995) Occurence of enzymes involved in biosynthesis of indole-3-acetic acid from indole-3-acetonitrile in plant-associated bacteria, Agrobacterium and Rhizobium. Proc Natl Acad Sci USA 92: 714-718
19. Layh N, Stolz A, Förster S, Effenberger F, Knackmuss H-J (1992) Enantioselective hydrolysis of O-acetylmandelonitrile to O-acetylmandelic acid by bacterial nitrilases. Arch Microbiol 158: 405-411
20. Layh N, Stolz A, Böhme J, Effenberger F, Knackmuss H-J (1994) Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates. J Biotechnol 33: 175-182
21. Layh N, Knackmuss H-J, Stolz A (1995) Enantioselective hydrolysis of ketoprofen amide by Rhodococcus sp. C3II and Rhodococcus erythropolis MP 50. Biotechnol Lett 17: 187-192
22. Lee WH, Kim K-J, Kim MG, Lee SB (1995) Enzymatic resolution of racemic ibuprofen esters: effects of organic cosolvents and temperature. J Ferment Bioeng 80: 613-615
23. Martinková L, Stolz A, Knackmuss H-J (1996) Enantioselectivity of the nitrile hydratase from Rhodococcus equi A4 towards substituted (R,S)-2-arylpropionitriles. Biotechnol Lett 18: 1073-1076
24. Masutomo S, Inoue A, Kumagai K, Murai R, Mitsuda S (1995) Enantioselective hydrolysis of (RS)-2-isopropyl-4′-chlorophenylacetonitrile by Pseudomonas sp. B21C9. Biosci Biotechnol Biochem 59: 720-722
25. Mauger J, Nagasawa T, Yamada H (1988) Nitrile hydratase-catalyzed production of isonicotinamide, picolinamide and pyrazinamide from 4-cyanopyridine, 2-cyanopyridine and cyanopyrazine in Rhodococcus rhodochrous J1. J Biotechnol 8: 87-96
26. Mayaux J-F, Cerbelaud E, Soubrier F, Faucher D, Pétré D (1990) Purification, cloning, and primary structure of an enantiomer-selective amidase from Brevibacterium sp. strain R312: structural evidence for genetic coupling with nitrile hydratase. J Bacteriol 172: 6764-6773
27. Mayaux J-F, Cerbelaud E, Soubrier F, Yeh P, Blanche F, Pétré D (1991) Purification, cloning, and primary structure of a new enantiomer-selective amidase from a Rhodococcus strain: structural evidence for a conserved genetic coupling with nitrile hydratase. J Bacteriol 173: 6694-6704
28. Nagasawa T, Yamada H (1990) Application of nitrile-converting enzymes for the production of useful compounds. Pure Appl Chem 62: 1441-1444
29. Nagasawa T, Ryuno K, Yamada H (1986) Nitrile hydratase of Brevibacterium R312 - Purification and characterization-. Biochem Biophys Res Comm 139: 1305-1312
30. Nagasawa T, Nanba H, Takeuchi K, Yamada H (1987) Nitrile hydratase of Pseudomonas chlororaphis B23-Purification and characterization. Eur J Biochem 162: 691-698
31. Nagasawa T, Mathew CD, Mauger J, Yamada H (1988) Nitrile hydratase-catalyzed production of nicotinamide from 3-cyanopyridine in Rhodococcus rhodochrous J1. Appl Environ Microbiol 54: 1766-1769
32. Nagasawa T, Takeuchi K, Yamada H (1991) Characterization of a new cobalt-containing nitrile hydratase purified from urea-induced cells of Rhodococcus rhodochrous J1. Eur J Biochem 196: 581-589
33. Payne M, Wu S, Fallon R, Tudor G, Stieglitz B, Turner I, Nelson M (1997) A stereoselective cobalt-containing nitrile hydratase. Biochemistry 36: 5447-5454
34. Phillips RS (1992) Temperature effects on stereochemistry of enzymatic reactions. Enzyme Microb Technol 14: 417-419
35. Rauscher K, Voigt J, Wilke I, Wilke K-T (1982) Chemische Tabellen und Rechentafeln für die analytische Praxis. 7. überarbeitete Auflage, Verlag Henoi Deutsch. Frankfurt am Main
36. Sugiura Y, Kuwahara J, Nagasawa T, Yamada H (1987) Nitrile hydratase: the first non-heme iron enzyme with a typical low-spin Fe(III)-active center. J Am Chem Soc 109: 5848-5850
37. Tani Y, Kurihara M, Nishise H (1989) Characterization of nitrile hydratase and amidase, which are responsible for the conversion of dinitriles to mononitriles, from Corynebacterium sp. Agric Biol Chem 53: 3151-3158
38. Yamada H, Kobayashi M (1996) Nitrile hydratase and its application to industrial production of acrylamide. Biosci Biotechnol Biochem 60: 1391-1400
39. Yamamoto K, Komatsu K-I (1991) Purification and characterization of nitrilase responsible for the enantioselective hydrolysis from Acinetobacter sp. AK 226. Agric Biol Chem 55: 1459-1466
40. Yamamoto K, Fujimatsu I, Komatsu K-I (1992) Purification and characterization of the nitrilase from Alcaligenes faecalis ATCC 8750 responsible for enantioselective hydrolysis of mandelonitrile. J Ferment Bioeng 73: 425-430