Directed evolution of Alcaligenes faecalis nitrilase

Enzyme and Microbial Technology

Volumn 47, Issue 4, 2010, Pages 140-146

  Schreiner, Ulrike ^a   Hecher, Bianca ^a   Obrowsky, Sascha ^a   Waich, Kerstin ^a   Klempier, Norbert ^a   Steinkellner, Georg ^a,b   Gruber, Karl ^b   Rozzell, J David ^c   Glieder, Anton ^a   Winkler, Margit ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b UNIVERSITY OF GRAZ   (Austria)

^c R and D Project Development and Management   (United States)

Author keywords

Directed evolution; Enzyme catalysis; Mutation; Nitrilase; PH stability

Indexed keywords

BIOCHEMISTRY; BIOTECHNOLOGY;

DIRECTED EVOLUTION; ENZYME CATALYSIS; MUTATION; NITRILASE; PH STABILITY;

PH;

2 PHENYLPROPIONITRILE; MANDELIC ACID; NITRILASE; PROPIONITRILE; UNCLASSIFIED DRUG;

ALCALIGENES FAECALIS; ARTICLE; CATALYSIS; ENANTIOMER; ENZYME ACTIVE SITE; ENZYME ENGINEERING; ENZYME SPECIFICITY; ENZYME STABILITY; ENZYME SUBSTRATE; EVOLUTION; MUTATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PH; POLYMERASE CHAIN REACTION;

ALCALIGENES FAECALIS;

EID: 77955282467     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2010.05.012     Document Type: Article

References (43)

1. Brenner C. Catalysis in the nitrilase superfamily. Curr Opin Struct Biol 2002, 12:775-782.
2. Sugai T., Yamazaki T., Yokoyama M., Ohta H. Biocatalysis in organic synthesis: the use of nitrile- and amide-hydrolyzing microorganisms. Biosci Biotech Biochem 1997, 61:1419-1427.
3. Kaul P., Banerjee U.C. Predicting enzyme behavior in nonconventional media: correlating nitrilase function with solvent properties. J Ind Microbiol Biotechnol 2008, 35:713-720.
4. Banerjee A., Kaul P., Banerjee U.C. Purification and characterization of an enantioselective arylacetonitrilase from Pseudomonas putida. Arch Microbiol 2006, 184:407-418.
5. DeSantis G., Wong K., Farwell B., Chatman K., Zhu Z., Tomlinson G., et al. Creation of a productive, highly enantioselective nitrilase through Gene Site Saturation Mutagenesis (GSSM). J Am Chem Soc 2003, 125:11476-11477.
6. DeSantis G, Chaplin JA, Chi E, Milan A, Short JM, Weiner D, et al. Nitrilases, 2004, US 2004002147 A1.
7. Wu S., Fogiel A.J., Petrillo K.L., Hann E.C., Mersinger L.J., DiCosimo R., et al. Protein engineering of Acidovorax facilis 72W nitrilase for bioprocess development. Biotechnol Bioeng 2007, 97:689-693.
8. Xie Z., Feng J., Garcia E., Bernett M., Yazbeck D., Tao J. Cloning and optimization of a nitrilase for the synthesis of (3S)-3-cyano-5-methyl hexanoic acid. J Mol Catal B: Enzym 2006, 41:75-80.
9. Payne MS, DiCosimo R, O'Keefe DP, Production of 3-hydroxycarboxylic acid using nitrilase; 2006, US 2006035352A1.
10. Wu S., Fogiel A.J., Petrillo K.L., Jackson R.E., Parker K.N., DiCosimo R., et al. Protein engineering of nitrilase for chemoenzymatic production of glycolic acid. Biotechnol Bioeng 2008, 99:717-720.
11. Nagasawa T., Mauger J., Yamada H. A novel nitrilase, arylacetonitrilase, of Alcaligenes faecalis JM3: purification and characterization. Eur J Biochem 1990, 194:765-772.
12. Kiziak C., Klein J., Stolz A. Influence of different carboxy-terminal mutations on the substrate-, reaction- and enantiospecificity of the arylacetonitrilase from Pseudomonas fluorescens EBC191. Protein Eng Des Sel 2007, 20:385-396.
13. Banerjee A., Dubey S., Kaul P., Barse B., Pietrowski M., Banerjee U.C. Enantioselective nitrilase from Pseudomonas putida: cloning, heterologous expression, and bioreactor studies. Mol Biotechnol 2009, 41:35-41.
14. Vorwerk S., Biernacki S., Hillebrand H., Janzik I., Müller A., Weiler E.W., et al. Enzymatic characterization of the recombinant Arabidopsis thaliana nitrilase subfamily encoded by the NIT2/NIT1/NIT3-gene cluster. Planta 2001, 212:508-516.
15. DeSantis G., Zhu Z., Greenberg W.A., Wong K., Chaplin J., Hanson S.R., et al. An enzyme library approach to biocatalysis: development of nitrilases for enantioselective production of carboxylic acid derivatives. J Am Chem Soc 2002, 124:9024-9025.
16. Kiziak C., Stolz A. Identification of amino acid residues responsible for the enantioselectivity and amide formation capacity of the arylacetonitrilase from Pseudomonas fluorescens EBC191. Appl Environ Microbiol 2009, 75:5592-5599.
17. Banerjee A., Sharma R., Banerjee U.C. The nitrile-degrading enzymes: current status and future prospects. Appl Microbiol Biotechnol 2002, 60:33-44.
18. Rustler S., Motejadded H., Altenbuchner J., Stolz A. Simultaneous expression of an arylacetonitrilase from Pseudomonas fluorescens and a (S)-oxynitrilase from Manihot esculenta in Pichia pastoris for the synthesis of (S)-mandelic acid. Appl Microbiol Biotechnol 2008, 80:87-97.
19. Rustler S., Stolz A. Isolation and characterization of a nitrile hydrolyzing acidotolerant black yeast-Exophiala oligosperma R1. Appl Microbiol Biotechnol 2007, 75:899-908.
20. Mateo C., Chmura A., Rustler S., van Rantwijk F., Stolz A., Sheldon R.A. Stabilisation of oxygen-labile nitrilases via co-aggregation with poly(ethyleneimine). Tetrahedron Asymm 2006, 17:320-323.
21. Kaul P., Stolz A., Banerjee U.C. Cross-linked amorphous nitrilase aggregates for enantioselective nitrile hydrolysis. Adv Syn Catal 2007, 349:2167-2176.
22. Kumaran D., Eswaramoorthy S., Gerchman S.E., Kycia H., Studier F.W., Swaminathan S. Crystal structure of a putative CN hydrolase from yeast. Protein Struct Funct Genet 2003, 52:283-291.
23. Sakai N., Tajika Y., Yao M., Watanabe N., Tanaka I. Crystal structure of hypothetical protein PH0642 from Pyrococcus horikoshii at 1.6Å Resolution. Protein Struct Funct Genet 2004, 57:869-873.
24. Notredame C., Higgins D.G., Heringa J. T-Coffee: a novel method for fast and accurate multiple sequence alignment. J Mol Biol 2000, 302:205-217.
25. Sali A., Blundell T.L. Comparative protein modelling by satisfaction of spatial restraints. J Mol Biol 1993, 234:779-815.
26. Arnold F.H. Directed evolution: creating biocatalysts for the future. Chem Eng Sci 1996, 51:5091-5102.
27. Varshavsky A. The N-end rule: functions, mysteries, uses. Proc Natl Acad Sci USA 1996, 93:12142-12149.
28. Kobayashi M., Izui H., Nagasawa T., Yamada H. 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 Nat Acad Sci USA 1993, 90:247-251.
29. Berthelot M. Rep Chim App 1859, 1:284.
30. Thuku R.N., Brady D., Benedik M.J., Sewell B.T. Microbial nitrilases: versatile, spiral forming, industrial enzymes. J Appl Microbiol 2009, 106:703-727.
31. Kim J.-S., Tiwari M.K., Moon H.-J., Jeya M., Ramu T., Oh D.-K., et al. Identification and characterization of a novel nitrilase from Pseudomonas fluorescens Pf-5. Appl Microbiol Biotechnol 2009, 83:273-283.
32. Yamamoto K., Fujimatsu I., Komatsu K. Purification and characterization of the nitrilase from Alcaligenes faecalis ATCC 8750 responsible for enantioselective hydrolysis of mandelonitrile. J Ferment Bioeng 1992, 73:425-430.
33. Ress-Löschke M, Friedrich T, Hauer B, Mattes R, Engels D. Method for producing chiral carboxylic acids from nitriles with the assistance of nitrilases or microorganisms which contain a gene for the nitrilase; 2005, US 6869783B1.
34. Singh R., Banerjee A., Kaul P., Barse B., Banerjee U.C. Release of an enantioselective nitrilase from Alcaligenes faecalis MTCC 126: a comparative study. Bioprocess Biosyst Eng 2005, 27:415-424.
35. Banerjee A., Kaul P., Banerjee U.C. Enhancing the catalytic potential of nitrilase from Pseudomonas putida for stereoselective nitrile hydrolysis. Appl Microbiol Biotechnol 2006, 72:77-87.
36. Rey P., Rossi J., Taillades J., Gros G., Nore O. Hydrolysis of nitriles using an immobilized nitrilase: applications to the synthesis of methionine hydroxy analogue derivatives. J Agric Food Chem 2004, 52:8155-8162.
37. Rustler S., Müller A., Windeisen V., Chmura A., Fernandes B.C.M., Kiziak C., et al. Conversion of mandelonitrile and phenylglycinenitrile by recombinant E. coli cells synthesizing a nitrilase from Pseudomonas fluorescens EBC191. Enzyme Microb Tech 2007, 40:598-606.
38. Fernandes B.C.M., Mateo C., Kiziak C., Chmura A., Wacker J., van Rantwijk F., et al. Nitrile hydratase activity of a recombinant nitrilase. Adv Syn Catal 2006, 348:2597-2603.
39. Yin L., Shan W., Jia X., Li X., Chan A.S.C. Ru-catalyzed enantioselective preparation of methyl (R)-o-chloromandelate and its application in the synthesis of (S)-Clopidogrel. J Organomet Chem 2009, 694:2092-2095.
40. Purkarthofer T., Skranc W., Schuster C., Griengl H. Potential and capabilities of hydroxynitrile lyases as biocatalysts in the chemical industry. Appl Microbiol Biot 2007, 76:309-320.
41. Griengl H., Hickel A., Johnson D.V., Schmidt M., Kratky C., Schwab H. Enzymatic cleavage and formation of cyanohydrins: a reaction of biological and synthetic relevance. Chem Commun 1997, 20:1933-1940.
42. Sosedov O., Matzer K., Bürger S., Kiziak C., Baum S., Altenbuchner J., et al. Construction of recombinant Escherichia coli catalyst which simultaneously express an (S)-oxynitrilase and different nitrilase variants for the synthesis of (S)-mandelic acid and (S)-mandelic amide from benzaldehyde and cyanide. Adv Synth Catal 2009, 351:1531-1538.
43. Pace H.C., Hodawadekar S.C., Draganescu A., Huang J., Bieganowski P., Pekarsky Y., et al. Crystal structure of the worm NitFhit Rosetta Stone protein reveals a Nit tetramer binding two Fhit dimers. Curr Biol 2000, 10:907-917.