Nitrilase activity screening on structurally diverse substrates: Providing biocatalytic tools for organic synthesis

Advanced Synthesis and Catalysis

Volumn 355, Issue 9, 2013, Pages 1763-1779

  Vergne Vaxelaire, Carine ^a,b,c   Bordier, Franck ^a,b,c   Fossey, Aurélie ^a,b,c   Besnard Gonnet, Marielle ^a   Debard, Adrien ^a   Mariage, Aline ^a   Pellouin, Virginie ^a   Perret, Alain ^a,b,c   Petit, Jean Louis ^a   Stam, Mark ^a,b,c   Salanoubat, Marcel ^a,b,c   Weissenbach, Jean ^a   De Berardinis, Véronique ^a   Zaparucha, Anne ^a,b,c  

^a DIF   (France)

^b CNRS   (France)

^c UNIVERSITÉ D EVRY VAL D ESSONNE   (France)

Author keywords

biocatalysis; building blocks; enzyme diversity; high throughput screening; nitrilases

Indexed keywords

EID: 84879195060     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201201098     Document Type: Article

References (64)

1. H. Velankar, K. G. Clarke, R. du Preez, D. A. Cowan, S. G. Burton, Trends Biotechnol. 2010, 28, 561-569
2. M.-X. Wang, Topics in Catalysis 2005, 35, 117-130
3. R. Singh, R. Sharma, N. Tewari, Geetanjali, D. S. Rawat, Chem. Biodiversity 2006, 3, 1279-1287
4. L. Martínková, V. Křen, Curr. Opin. Chem. Biol. 2010, 14, 1-8
5. J.-S. Gong, Z.-M. Lu, H. Li, J.-S. Shi, Z.-M. Zhou, Z.-H. Xu, Microbial Cell Factories 2012, 11, 142-185.
6. C. Brenner, Curr. Opin. Struct. Biol. 2002, 12, 775-782
7. C. O'Reilly, P. D. Turner, J. Appl. Microbiol. 2003, 95, 1161-1174.
8. G. DeSantis, Z. Zhu, W. A. Greenberg, K. Wong, J. Chaplin, S. R. Hanson, B. Farwell, L. W. Nicholson, C. L. Rand, D. P. Weiner, D. E. Robertson, M. J. Burk, J. Am. Chem. Soc. 2002, 124, 9024-9025
9. D. E. Robertson, J. A. Chaplin, G. DeSantis, M. Podar, M. Madden, E. Chi, T. Richardson, A. Milan, M. Miller, D. P. Weiner, K. Wong, J. McQuaid, B. Farwell, L. A. Preston, X. Tan, M. A. Snead, M. Keller, E. Mathur, P. L. Kretz, M. J. Burk, J. M. Short, Appl. Environ. Microbiol. 2004, 70, 2429-2436
10. J. L. Seffernick, S. K. Samanta, T. Man Louie, L. P. Wackett, M. Subramanian, J. Biotechnol. 2009, 143, 17-26
11. P. Kaul, A. Banerjee, S. Mayilray, U. C. Banerjee, Tetrahedron: Asymmetry 2004, 15, 207-211
12. D. Brady, A. Beeton, J. Zeevaart, C. Kgaje, F. van Rantwijk, R. A. Sheldon, Appl. Microbiol. Biotechnol. 2004, 64, 76-85
13. Z. Xie, J. Feng, E. Garcia, M. Bernett, D. Yazbeck, J. Tao, J. Mol. Cat. B: Enzym. 2006, 41, 75-80
14. D. Zhu, C. Mukherjee, Y. Yang, B. E. Rios, D. T. Gallagher, N. N. Smith, E. R. Biehl, L. Hua, J. Biotechnol. 2008, 133, 327-333
15. J.-S. Kim, M. Kumar Tiwari, H.-J. Moon, M. Jeya, T. Ramu, D.-K. Oh, I.-W. Kim, J.-K. Lee, Appl. Microbiol. Biotechnol. 2009, 83, 273-283.
16. E. Pelletier, A. Kreimeyer, S. Bocs, Z. Rouy, G. Gyapay, R. Chouari, D. Riviere, A. Ganesan, P. Daegelen, A. Sghir, G. N. Cohen, C. Medigue, J. Weissenbach, D. Le Paslier, J. Bacteriol. 2008, 190, 2572-2579.
17. J.-L. Reymond, in: Enzyme Assays (Ed.:, J.-L. Reymond,), Wiley-VCH, Weinheim, 2006, pp 105-115.
18. A. Kreimeyer, A. Perret, C. Lechaplais, D. Vallenet, C. Médigue, M. Salanoubat, J. Weissenbach, J. Biol. Chem. 2007, 282, 7191-7197.
19. S. V. Pawar, V. S. Meena, S. Kaushik, A. Kamble, S. Kumar, Y. Chisti, U. C. Banerjee, 3Biotech. 2012, 2, 319-326
20. A. Petrickova, A. B. Vesela, L. Martínková, MECP12 Graz, 2012, Poster 16.
21. This new enzymatic reaction has been edited in RHEA database (EMBL-EBI European Bioinformatics Institute, http://www.ebi.ac.uk/); a) RHEA:34879; b) RHEA:34859; c) RHEA:34855.
22. For example:, C. Kiziak, D. Conradt, A. Stolz, R. Mattes, J. Klein, Microbiology 2005, 151, 3639-3648.
23. C. Mukherjee, D. Zhu, E. R. Biehl, L. Hua, Eur. J. Org. Chem. 2006, 5238-5242.
24. C. Gaulon, R. Dhal, T. Chapin, V. Maisonneuve, G. Dujardin, J. Org. Chem. 2004, 69, 4192-4202
25. Y. Tamura, Y. Shirouchi, J.-i. Minamikawa, J.-i. Haruta, Chem. Pharm. Bull. 1985, 33, 551-556
26. M. T. Edgar, G. R. Pettit, T. H. Smith, J. Org. Chem. 1978, 43, 4115-4120.
27. K. Inoue, Y. Ishikawa, S. Nishiyama, Org. Lett. 2010, 12, 436-439
28. O. Rogel, J.-M. Rondeau, H. Ruegger, O. Simic, F. Sirockin, M. Tintelnot-Blomley, WO Patent, 140980, 2007.
29. M. Calmes, F. Escale, J. Martinez, Tetrahedron: Asymmetry 2002, 13, 293-296.
30. E. W. Della, A. M. Knill, Aust. J. Chem. 1994, 47, 1833-1841
31. Y. Sekiyama, N. Palaniappan, K. A. Reynolds, H. Osada, Tetrahedron 2003, 59, 7465-7471.
32. D. Zhu, C. Mukherjee, E. R. Biehl, L. Hua, Adv. Synth. Catal. 2007, 349, 1667-1670.
33. M. Winkler, A. C. Knall, M. R. Kulterer, N. Klempier, J. Org. Chem. 2007, 72, 7423-7426.
34. T. Beard, M. A. Cohen, J. S. Parratt, N. J. Turner, Tetrahedron: Asymmetry 1993, 4, 1085-1104.
35. For industrial example, see:, S. Bergeron, D. A. Chaplin, J. H. Edwards, B. S. W. Ellis, C. L. Hill, K. Holt-Tiffin, J. R. Knight, T. Mahoney, A. P. Osborne, G. Ruecroft, Org. Process Res. Dev. 2006, 10, 661-665.
36. P. Rey, J.-C. Rossi, J. Taillades, G. Gros, O. Nore, J. Agric. Food Chem. 2004, 52, 8155-8162.
37. S. Bayer, C. Birkemeyer, M. Ballschmitter, Appl. Microbiol. Biotechnol. 2011, 89, 91-98.
38. Z.-Q. Liu, F.-F. Li, F. Cheng, T. Zhang, Z.-Y. You, J.-M. Xu, Y.-P. Xue, Y.-G. Zheng, Y.-C. Shen, Biotechnol. Prog. 2011, 27, 698-705.
39. O. V. Shekhter, O. B. Kuklenkova, N. L. Sergovskaya, Y. S. Tsizin, Chem. Heterocycl. Compds. 1993, 29, 170-173.
40. U. Heinemann, D. Engels, S. Bürger, C. Kiziak, R. Mattes, A. Stolz, Appl. Environ. Microbiol. 2003, 69, 4359-4366.
41. P. Mueller, K. Egorova, C. E. Vorgias, E. Boutou, H. Trauthwein, S. Verseck, G. Antranikian, Prot. Express. Purif. 2006, 47, 672-681.
42. Z.-J. Zhang, J.-H. Xu, Y.-C. He, L.-M. Ouyang, Y.-Y. Liu, Bioproc. Biosyst. Eng. 2011, 34, 315-322.
43. T. Nagasawa, J. Mauger, H. Yamada, Eur. J. Biochem. 1990, 194, 765-772.
44. C.-S. Zhang, Z.-J. Zhang, C.-X. Li, H.-L. Yu, G.-W. Zheng, J.-H. Xu, Appl. Microbiol. Biotechnol. 2012, 95, 91-99.
45. D. M. Stalker, L. D. Malyj, K. E. McBride, J. Biol. Chem. 1988, 263, 6310-6314.
46. M. Kobayashi, H. Komeda, N. Yanaka, T. Nagasawa, H. Yamada, J. Biol. Chem. 1992, 267, 20746-20751.
47. M. Kobayashi, N. Yanaka, T. Nagasawa, H. Yamada, Biochemistry 1992, 31, 9000-9007.
48. Y. Kato, K. Nakamura, H. Sakiyama, S. G. Mayhew, Y. Asano, Biochemistry 2000, 39, 800-809.
49. O. Kaplan, K. Bezouška, A. Malandra, A. B. Veselá, A. Petříčková, J. Felsberg, A. Rinágelová , V. Křen, L. Martínková, Biotechnol. Lett. 2011, 33, 309-312.
50. S. Rozen, H. Skaletsky, Meth. Mol. Biol. 2000, 132, 365-386.
51. C. Aslanidis, P. J. de Jong, Nucleic Acids Res. 1990, 18, 6069-6074.
52. T. Itoh, K. Mitsukura, W. Kanphai, Y. Takagi, H. Kihara, H. Tsukube, J. Org. Chem. 1997, 62, 9165-9172.
53. S. Kamila, D. Zhu, E. R. Biehl, L. Hua, Org. Lett. 2006, 8, 4429-4431.
54. P. G. Williams, W. Y. Yoshida, R. E. Moore, V. J. Paul, J. Nat. Prod. 2002, 65, 29-31.
55. A. Benalil, B. Carboni, M. Vaultier, Tetrahedron 1991, 47, 8177-8194.
56. P. Camps, D. Munoz-Torrero, L. Sanchez, Tetrahedron: Asymmetry 2004, 15, 311-332.
57. I. S. Mitchell, K. L. Spencer, P. Stengel, Y. Han, N. C. Kallan, M. Munson, G. P. Vigers, J. Blake, A. Piscopio, J. Josey, S. Miller, D. Xiao, R. Xu, C. Rao, B. Wang, A. L. Bernacki, WO Patent 051304 A2, 2005.
58. G. Dujardin, S. Rossignol, S. Molato, E. Brown, Tetrahedron 1994, 50, 9037-9050.
59. X.-Q. Yu, T. Shirai, Y. Yamamoto, N. Miyaura, Chem. Asian J. 2011, 6, 932-937.
60. K. Curry, M. J. Peet, D. S. K. Magnuson, H. McLennan, J. Med. Chem. 1988, 31, 864-867.
61. H. C. Berk, T. S. Franczyk II, R. B. Weisenfeld, D. A. Morgenstern, J. P. Arhancet, W. L. Moench Jr, J. C. Peterson, U.S. Patent 19565 A1, 2002
62. K. Kawashiro, S. Morimoto, H. Yoshida, Bull. Chem. Soc. Jpn. 1983, 56, 792-795.
63. A. Dereeper, V. Guignon, G. Blanc, S. Audic, S. Buffet, F. Chevenet, J.-F. Dufayard, S. Guindon, V. Lefort, M. Lescot, J.-M. Claverie, O. Gascuel, Nucleic Acids Res. 2008, 36, w 465 -w 469.
64. H. Hillebrand, D. Bartling, E. W. Weiler, Plant Mol. Biol. 1998, 36, 89-99.