Construction and application of variants of the pseudomonas fluorescens EBC191 arylacetonitrilase for increased production of acids or amides

Applied and Environmental Microbiology

Volumn 76, Issue 11, 2010, Pages 3668-3674

  Sosedov, Olga ^a   Baum, Stefanie ^a   Bürger, Sibylle ^a   Matzer, Kathrin ^a   Kiziak, Christoph ^a,b   Stolz, Andreas ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b LONZA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

A PLANTS; AMIDE FORMATION; AMINO ACID RESIDUES; AMINO TERMINUS; C TERMINUS; CYSTEINE RESIDUES; HIGH YIELD; HYDROXYNITRILE LYASES; MANDELIC ACID; NITRILASE; PSEUDOMONAS FLUORESCENS; RECOMBINANT PLASMID; SERINE RESIDUES; SINGLE MUTATION; WHOLE CELL BIOCATALYSTS;

ALDEHYDES; AMINO ACIDS; CYANIDES; ENZYMES; ESCHERICHIA COLI; ORGANIC ACIDS; PHOSPHATASES;

AMIDES;

AMIDE; BENZALDEHYDE; BENZALDEHYDE DERIVATIVE; CARBOXYLIC ACID; CYANIDE; HYDROLASE; MANDELIC ACID DERIVATIVE; MUTANT PROTEIN; RECOMBINANT PROTEIN;

ACID; BACTERIUM; CATALYSIS; ENZYME ACTIVITY; MOLECULAR ANALYSIS; NUCLEIC ACID;

AMINO ACID SUBSTITUTION; ARTICLE; BACTERIUM TRANSFORMATION; ENZYME SPECIFICITY; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; METABOLISM; PLASMID; PSEUDOMONAS FLUORESCENS; SITE DIRECTED MUTAGENESIS;

AMIDES; AMINO ACID SUBSTITUTION; AMINOHYDROLASES; BENZALDEHYDES; CARBOXYLIC ACIDS; CYANIDES; ESCHERICHIA COLI; MANDELIC ACIDS; MUTAGENESIS, SITE-DIRECTED; MUTANT PROTEINS; PLASMIDS; PSEUDOMONAS FLUORESCENS; RECOMBINANT PROTEINS; SUBSTRATE SPECIFICITY; TRANSFORMATION, BACTERIAL;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; PSEUDOMONAS FLUORESCENS;

EID: 77953039782     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.00341-10     Document Type: Article

References (36)

1. Brenner, C. 2002. Catalysis in the nitrilase superfamily. Curr. Opin. Struct. Biol. 12: 775-782.
2. Effenberger, F., and S. Osswald. 2001. Enantioselective hydrolysis of (RS)-2-fluoroacetonitriles using nitrilase from Arabidopsis thaliana. Tetrahedron Asymmetry 12: 279-285.
3. Fernandes, B. C. M., C. Mateo, C. Kiziak, J. Wacker, A. Chmura, F. van Rantwijk, A. Stolz, and R. A. Sheldon. 2006. Nitrile hydratase activity of a recombinant nitrilase. Adv. Synth. Catal. 348: 2597-2603.
4. Foerstner, K. U., T. Doerks, J. Muller, J. Raes, and P. Bork. 2008. A nitrile hydratase in the eukaryote Monosiga brevicollis. PLoS One 3: e3976. doi: 10.1371/journal.pone.0003976.
5. Heinemann, U., C. Kiziak, S. Zibek, N. Layh, M. Schmidt, H. Griengl, and A. Stolz. 2003. Conversion of aliphatic 2-acetoxynitriles by nitriles hydrolysing bacteria. Appl. Microbiol. Biotechnol. 63: 274-281.
6. Horton, R. M., H. D. Hunt, S. N. Ho, J. K. Pullen, and L. R. Pease. 1989. Engineering of hybrid genes without use of restriction enzymes: gene splicing by overlap extension. Gene 77: 61-68.
7. Jenrich, R., I. Trompetter, S. Bak, C. E. Olsen, B. Lindberg Møller, and M. Piotrowski. 2007. Evolution of heteromeric nitrilase complexes in Poaceae with new functions in nitrile metabolism. Proc. Natl. Acad. Sci. U. S. A. 104: 18848-18853.
8. Kiziak, C., D. Conradt, A. Stolz, R. Mattes, and J. Klein. 2005. Nitrilase from Pseudomonas fluorescens EBC191: cloning and heterologous expression of the gene and biochemical characterization of the recombinant enzyme. Microbiology 151: 3639-3648.
9. Kiziak, C., J. Klein, and A. Stolz. 2007. Influence of different carboxyterminal mutations on the substrate-, reaction-, and enantiospeciflcity of the arylacetonitrilase from Pseudomonas fluorescens EBC191. Protein Eng. Des. Sel. 20: 385-396. (Pubitemid 47428965)
10. Kiziak, C., and A. Stolz. 2009. Identification of amino acid residues which are responsible for the enatioselectivity and amide formation capacity of the arylacetonitrilase from Pseudomonas fluorescens EBC 191. Appl. Environ. Microbiol. 75: 5592-5599.
11. Kobayashi, M., H. Izui, T. Nagasawa, and H. Yamada. 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. U. S. A. 90: 247-251.
12. Kobayashi, M., H. Komeda, N. Yanaka, T. Nagasawa, and H. Yamada. 1992. Nitrilase from Rhodococcus rhodochrous J1. Sequencing and overexpression of the gene and identification of an essential cysteine residue. J. Biol. Chem. 267: 20746-20751.
13. Kobayashi, M., and S. Shimizu. 1994. Versatile nitrilases: nitrile-hydrolysing enzymes. FEMS Microbiol. Lett. 120: 217-224.
14. Kobayashi, M., and S. Shimizu. 1998. Metalloenzyme nitrile hydratase: structure, regulation, and application to biotechnology. Nat. Biotechnol. 16: 733-736.
15. Layh, N., A. Stolz, S. Förster, F. Effenberger, and H.-J. Knackmuss. 1992. Enantioselective hydrolysis of O-acetylmandelonitrile to O-acetylmandelic acid by bacterial nitrilases. Arch. Microbiol. 158: 405-411.
16. Liese, A., K. Seelbach, and C. Wandrey. 2006. Industrial biotransformations, 2nd ed. Wiley-VCH, Weinheim, Germany.
17. Martinková, L., and V. Křen. 2002. Nitrile- and amide-converting microbial enzymes: stereo-, regio- and chemoselectivity. Biocatal. Biotrans. 20: 79-93.
18. Martinková, L., and V. Mylerová. 2003. Synthetic applications of nitrileconverting enzymes. Curr. Org. Chem. 7: 1279-1295.
19. Mateo, C., A. Chmura, S. Rustler, F. van Rantwijk, A. Stolz, and R. A. Sheldon. 2006. Synthesis of enantiomerically pure (S)-mandelic acid using an oxynitrilase-nitrilase hienzymatic cascade. A nitrilase surprisingly shows nitrile hydratase activity. Tetrahedron Asymmetry 17: 320-323.
20. O'Reilly, C., and P. D. Turner. 2003. The nitrilase family of CN hydrolysing enzymes-a comparative study. J. Appl. Microbiol. 95: 1161-1174.
21. Pace, H. C., and C. Brenner. 2001. The nitrilase superfamily: classification, structure and function. Genome Biol. 2: 0001.1-0001.9.
22. Panova, A., L. J. Mersinger, Q. Liu, T. Foo, D. C. Roe, W. L. Spillan, A. E. Sigmund, A. Ben-Bassat, L. W. Wagner, D. P. O'Keefe, S. Wu, K. L. Perrillo, M. S. Payne, S. T. Breske, F. G. Gallagher, and R. DiCosimo. 2007. Chemoenzymatic synthesis of glycolic acid. Adv. Synth. Catal. 349: 1462-1474.
23. Piotrowski, M., S. Schönfelder, and E. W. Weiler. 2001. The Arabidapsis thaliana isogene NIT4 and its orthologs in tobacco encode beta-cyano-Lalanine hydratase/nitrilase. J. Biol. Chem. 276: 2616-2621.
24. Rustler, S., A. Müller, V. Windeisen, A. Chmura, B. C. M. Fernandes, C. Kiziak, and A. Stolz. 2007. Conversion of mandelonitrile and phenylglycinenitrile by recombinant E. coli cells synthesizing a nitrilase from Pseudomonas fluorescens EBC191. Enzyme Microb. Technol. 40: 598-606.
25. Sambrook, J., E. F. Fritsch, and T. Maniatis. 1989. Molecular cloning: a laboratory manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
26. Schulze, B. 2002. Hydrolysis and formation of C-N bonds, p. 699-715. In K. Drauz and H. Waldmann (ed.), Enzyme catalysis in organic synthesis, vol. II. Wiley-VCH, Weinheim, Germany.
27. Singh, R., R. Sharma, N. Tewari, Geetanjali, and D. S. Rawat. 2006. Nitrilase and its application as a green catalyst. Chem. Biodivers. 3: 1279-1297.
28. Sosedov, O., K. Matzer, S. Bürger, C. Kiziak, S. Baum, J. Altenbuchner, A. Chmura, F. van Randwijk, and A. Stolz. 2009. Construction of recombinant Escherichia coli catalysts which simultaneously express an (S)-oxynitrilase and different nitrilase variants for the synthesis of (S)-mandelic acid and (S)-mandeloamide from benzaldehyde and cyanide. Adv. Synth. Catal. 351: 1531-1538.
29. Stevenson, D. E., R. Feng, and A. C. Storer. 1990. Detection of covalent enzyme-substrate complexes of nitrilase by ion-spray mass spectroscopy. FEBS Lett. 277: 112-114.
30. Thuku, R. N., D. Brady, M. J. Benedik, and B. T. Sewell. 2009. Microbial nitrilases: versatile, spiral forming, industrial enzymes. J. Appl. Microbiol. 106: 703-727.
31. Thuku, R. N., B. W. Weber, A. Varsani, and B. T. Sewell. 2007. Posttranslational cleavage of recombinantly expressed nitrilase from Rhodococcus rhodochrous Jl yields a stable, active helical form. FEBS J. 274: 2099-2108.
32. Vieira, J., and J. Messing. 1982. The pUC plasmids, an M13mp7-derived system for insertion mutagenesis and sequencing with synthetic universal primers. Gene 19: 259-268. (Pubitemid 13201666)
33. Wu, S., A. J. Fogiel, K. L. Petrillo, E. C. Hann, L. J. Mersinger, R. DiCosimo, D. P. O'Keefe, A. Ben-Bassat, and M. S. Payne. 2007. Protein engineering of Acidovorax facilis 72W nitrilase for bioprocess development. Biotechnol. Bioeng. 97: 689-693.
34. Wu, S., A. J. Fogiel, K. L. Petrillo, R. E. Jackson, K. N. Parker, R. DiCosimo, A. Ben-Bassat, D. P. O'Keefe, and M. S. Payne. 2008. Protein engineering of nitrilase for chemoenzymatic production of glycolic acid. Biotechnol. Bioeng. 99: 717-720.
35. Yamamoto, K., I. Fujimatsu, and K.-I. Komatsu. 1992. Purification and characterization of the nitrilase from Alcaligenes faecalis ATCC 8750 responsible for enantioselective hydrolysis of mandelonitrile. J. Ferment. Bioeng. 73: 425-430.
36. Yamamoto, K., K. Oishi, I. Fujimatsu, and K.-I. Komatsu. 1991. Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750. Appl. Environ. Microbiol. 57: 3028-3032.