A nitrilase from a metagenomic library acts regioselectively on aliphatic dinitriles

Applied Microbiology and Biotechnology

Volumn 89, Issue 1, 2011, Pages 91-98

  Bayer, Sally ^a   Birkemeyer, Claudia ^a   Ballschmiter, Meike ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Aliphatic nitrilase; Dinitrile; Metagenome; Regioselectivity

Indexed keywords

BIOCHEMICAL PROPERTIES; CINNAMONITRILES; DINITRILE; FINE CHEMICALS; METAGENOMES; METAGENOMIC LIBRARIES; NITRILASE; NITRILE GROUPS; PHARMACEUTICAL PRODUCTS; PIPERIDONE; STEREOCHEMICAL ANALYSIS;

ESCHERICHIA COLI; REGIOSELECTIVITY;

CYANIDES;

1,5 DIMETHYL 2 PIPERIDONE; 4 CYANOPENTANOIC ACID; ALIPHATIC COMPOUND; ALIPHATIC DINITRILE; CARBOXYLIC ACID DERIVATIVE; CYANOCARBOXYLIC ACID; DINITRILE 2 METHYLGLUTARONITRILE; NITRILASE; NITRILE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

BIOCHEMICAL COMPOSITION; COLIFORM BACTERIUM; ENZYME ACTIVITY; GENOME; HYDROLYSIS; PROTEIN;

ARTICLE; BIOCHEMISTRY; ESCHERICHIA COLI; GENE; GENE EXPRESSION; METAGENOMICS; NIT1 GENE; NONHUMAN; NUCLEOTIDE SEQUENCE; STEREOCHEMISTRY;

AMINO ACID SEQUENCE; AMINOHYDROLASES; BACTERIA; BACTERIAL PROTEINS; CLONING, MOLECULAR; KINETICS; METAGENOMICS; MOLECULAR SEQUENCE DATA; NITRILES; RECOMBINANT PROTEINS; SEQUENCE ALIGNMENT; SOIL MICROBIOLOGY; SUBSTRATE SPECIFICITY; WATER MICROBIOLOGY;

ESCHERICHIA COLI;

EID: 78651091531     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-010-2831-9     Document Type: Article

References (35)

1. QA Almatawah R Cramp DA Cowan 1999 Characterization of an inducible nitrilase from a thermophilic Bacillus Extremophiles 3 283 291 1:CAS:528:DyaK1MXotFGrtr0%3D 10.1007/s007920050129
2. SF Altschul TL Madden AA Schaffer J Zhang Z Zhang W Miller DJ Lipman 1997 Gapped BLAST and PSI-BLAST: a new generation of protein database search programs Nucleic Acids Res 25 3389 3402 1:CAS:528:DyaK2sXlvFyhu7w%3D 10.1093/nar/25.17.3389 (Pubitemid 27359211)
3. A Banerjee R Sharma UC Banerjee 2003 A rapid and sensitive fluorometric assay method for the determination of nitrilase activity Biotechnol Appl Biochem 37 289 293 1:CAS:528:DC%2BD3sXktF2htLk%3D 10.1042/BA20020106 (Pubitemid 36713037)
4. C Bengisgarber AL Gutman 1989 Selective hydrolysis of dinitriles into cyano-carboxylic acids by Rhodococcus rhodochrous N.C.I.B.11216 Appl Microbiol Biotechnol 32 11 16 1:CAS:528:DyaK3cXpsFagsw%3D%3D
5. MM Bradford 1976 A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal Biochem 72 248 254 1:CAS:528:DyaE28XksVehtrY%3D 10.1016/0003-2697(76)90527- 3
6. S Chauhan S Wu S Blumerman RD Fallon JE Gavagan R DiCosimo MS Payne 2003 Purification, cloning, sequencing and over-expression in Escherichia coli of a regioselective aliphatic nitrilase from Acidovorax facilis 72 W Appl Microbiol Biotechnol 61 118 122 1:CAS:528:DC%2BD3sXit12mtr0%3D
7. FB Cooling SK Fager RD Fallon PW Folsom FG Gallagher JE Gavagan EC Hann FE Herkes RL Phillips A Sigmund LW Wagner W Wu R DiCosimo 2001 Chemoenzymatic production of 1, 5-dimethyl-2-piperidone J Mol Catal B Enzym 11 295 306 1:CAS:528:DC%2BD3MXptlSltQ%3D%3D 10.1016/S1381-1177(00)00150-8 (Pubitemid 32117623)
8. K Das AK Mukherjee 2007 Crude petroleum-oil biodegradation efficiency of Bacillus subtilis and Pseudomonas aeruginosa strains isolated from a petroleum-oil contaminated soil from North-East India Bioresour Technol 98 1339 1345 1:CAS:528:DC%2BD2sXjtFWk 10.1016/j.biortech.2006.05.032 (Pubitemid 46014609)
9. F Effenberger S Osswald 2001 Enantioselective hydrolysis of (R, S)-2-fluoroacetonitriles using nitrilase from Arabidopsis thaliana Tetrahedron Asym 12 279 285 1:CAS:528:DC%2BD3MXitVOjtr0%3D 10.1016/S0957-4166(01)00034-9 (Pubitemid 32232202)
10. EM Gabor EJ de Vries DB Janssen 2003 Efficient recovery of environmental DNA for expression cloning by indirect extraction methods FEMS Microbiol Ecol 44 153 163 1:CAS:528:DC%2BD3sXjtFWrsr4%3D 10.1016/S0168-6496(02)00462-2 (Pubitemid 36423411)
11. JE Gavagan SK Fager RD Fallon PW Folsom FE Herkes A Eisenberg EC Hann R DiCosimo 1998 Chemoenzymic production of lactams from aliphatic alpha, omega-dinitriles J Org Chem 63 4792 4801 1:CAS:528:DyaK1cXksVKqtbw%3D 10.1021/jo9804386
12. JE Gavagan R DiCosimo A Eisenberg sK Fager PW Folsom EC Hann KJ Schneider RD Fallon 1999 A Gram-negative bacterium producing a heat-stable nitrilase highly active on aliphatic dinitriles Appl Microbiol Biotechnol 52 654 659 1:CAS:528:DyaK1MXntlOisr0%3D 10.1007/s002530051574 (Pubitemid 29526156)
13. Greiner-Stöffele T, Struhalla M, Ballschmiter M, Czaja R (2008) Expressionsvektor EP 08021794.6
14. SK Gupta R Kumari O Prakash R Lal 2008 Pseudomonas panipatensis sp. nov., isolated from an oil-contaminated site Int J Syst Evol Microbiol 58 1339 1345 1:CAS:528:DC%2BD1cXovFeitLk%3D 10.1099/ijs.0.65401-0
15. EC Hann AE Sigmund SM Hennessey JE Gavagan DR Short A Ben Bassat S Chauhan RD Fallon MS Payne R DiCosimo 2002 Optimization of an immobilized-cell biocatalyst for production of 4-cyanopentanoic acid Org Process Res Dev 6 492 496 1:CAS:528:DC%2BD38XjtVKgu7o%3D 10.1021/op025515k
16. U Heinemann D Engels S Burger C Kiziak R Mattes A Stolz 2003 Cloning of a nitrilase gene from the cyanobacterium Synechocystis sp. strain PCC6803 and heterologous expression and characterization of the encoded protein Appl Environ Microbiol 69 4359 4366 1:CAS:528:DC%2BD3sXmsFWrsrk%3D 10.1128/AEM.69.8.4359- 4366.2003 (Pubitemid 36992887)
17. JS Kim MK Tiwari HJ Moon M Jeya T Ramu DK Oh IW Kim JK Lee 2009 Identification and characterization of a novel nitrilase from Pseudomonas fluorescens Pf-5 Appl Microbiol Biotechnol 83 273 283 1:CAS:528: DC%2BD1MXltlaqsLs%3D 10.1007/s00253-009-1862-6
18. SW Kimani VB Agarkar DA Cowan MF Sayed BT Sewell 2007 Structure of an aliphatic amidase from Geobacillus pallidus RAPc8 Acta Crystallogr D Biol Crystallogr 63 1048 1058 10.1107/S090744490703836X (Pubitemid 47480517)
19. K Kimbara T Hashimoto M Fukuda T Koana M Takagi M Oishi K Yano 1989 Cloning and sequencing of two tandem genes involved in degradation of 2, 3-dihydroxybiphenyl to benzoic acid in the polychlorinated biphenyl-degrading soil bacterium Pseudomonas sp. strain KKS102 J Bacteriol 171 2740 2747 1:CAS:528:DyaK3cXkvFGltw%3D%3D
20. N Klempier A de Raadt K Faber H Grieng 1991 Selective transformation of nitriles into amides and carboxylic acids by an immobilized nitrilase Tetrahedron Lett 32 341 344 1:CAS:528:DyaK3MXit1ygtro%3D 10.1016/S0040-4039(00) 92623-6
21. M Kobayashi T Nagasawa H Yamada 1988 Regiospecific hydrolysis of dinitrile compounds by nitrilase from Rhodococcus rhodochrous J1 Appl Microbiol Biotechnol 29 231 233 1:CAS:528:DyaL1cXlvVykt7g%3D
22. M Kobayashi N Yanaka T Nagasawa H Yamada 1990 Purification and characterization of a novel nitrilase of Rhodococcus rhodochrous K22 that acts on aliphatic nitriles J Bacteriol 172 4807 4815 1:CAS:528:DyaK3cXls1Orsbw%3D
23. S Levy-Schil F Soubrier AM Crutz-Le Coq D Faucher J Crouzet D Petre 1995 Aliphatic nitrilase from a soil-isolated Comamonas testosteroni sp.: gene cloning and overexpression, purification and primary structure Gene 161 15 20 1:CAS:528:DyaK2MXotVakt70%3D 10.1016/0378-1119(95)00242-X
24. Liese A, Seelbach K, Wandrey C (2006) Industrial biotransformations. Wiley VDH
25. L Martinkova V Vejvoda V Kren 2008 Selection and screening for enzymes of nitrile metabolism J Biotechnol 133 318 326 1:CAS:528:DC%2BD1cXhtlegtg%3D%3D 10.1016/j.jbiotec.2007.10.011 (Pubitemid 350299600)
26. C O'Reilly PD Turner 2003 The nitrilase family of CN hydrolysing enzymes-a comparative study J Appl Microbiol 95 1161 1174 10.1046/j.1365-2672. 2003.02123.x (Pubitemid 37506103)
27. HC Pace C Brenner 2001 The nitrilase superfamily: classification, structure and function Genome Biol 2 1 9 10.1186/gb-2001-2-1-reviews0001
28. DE Robertson JA Chaplin G DeSantis M Podar M Madden E Chi T Richardson A Milan M Miller DP Weiner K Wong J McQuaid B Farwell LA Preston X Tan MA Snead M Keller E Mathur PL Kretz MJ Burk JM Short 2004 Exploring nitrilase sequence space for enantioselective catalysis Appl Environ Microbiol 70 2429 2436 1:CAS:528:DC%2BD2cXjtlOhs7g%3D 10.1128/AEM.70.4.2429-2436.2004 (Pubitemid 38500548)
29. PH Roy SG Tetu A Larouche L Elbourne S Tremblay Q Ren R Dodson D Harkins R Shay K Watkins Y Mahamoud IT Paulsen 2010 Complete genome sequence of the multiresistant taxonomic outlier Pseudomonas aeruginosa PA7 PLoS ONE 5 e8842 10.1371/journal.pone.0008842
30. T Sugai T Yamazaki M Yokoyama H Ohta 1997 Biocatalysis in organic synthesis: the use of nitrile- and amide-hydrolyzing microorganisms Biosci Biotechnol Biochem 61 1419 1427 1:CAS:528:DyaK2sXmsFehs78%3D 10.1271/bbb.61.1419
31. SK Taylor NH Chmiel LJ Simons JR Vyvyan 1996 Conversion of hydroxy nitriles to lactones using Rhodococcus rhodochrous whole cells J Org Chem 61 9084 9085 1:CAS:528:DyaK28XnsVCgtrw%3D 10.1021/jo9616623 (Pubitemid 27067085)
32. JD Thompson DG Higgins TJ Gibson 1994 CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice Nucleic Acids Res 22 4673 4680 1:CAS:528:DyaK2MXitlSgu74%3D 10.1093/nar/22.22.4673
33. K Yamamoto I Fujimatsu K 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 1:CAS:528:DyaK38XkvVGktrk%3D 10.1016/0922-338X(92)90131-D
34. D Zhu C Mukherjee ER Biehl L Hua 2007 Nitrilase-catalyzed selective hydrolysis of dinitriles and green access to the cyanocarboxylic acids of pharmaceutical importance Adv Synth Catal 349 1667 1670 1:CAS:528: DC%2BD2sXos1Cqu7s%3D 10.1002/adsc.200700067
35. D Zhu C Mukherjee Y Yang BE Rios DT Gallagher NN Smith ER Biehl L Hua 2008 A new nitrilase from Bradyrhizobium japonicum USDA 110. Gene cloning, biochemical characterization and substrate specificity J Biotechnol 133 327 333 1:CAS:528:DC%2BD1cXhtlegtw%3D%3D 10.1016/j.jbiotec.2007.10.001 (Pubitemid 350299598)