Biocatalytic application of nitrilases from Fusarium solani O1 and Aspergillus niger K10

被引:16
作者
Winkler, Margit [2 ]
Kaplan, Ondrej [1 ]
Vejvoda, Vojtech [1 ]
Klempier, Norbert [2 ]
Martinkova, Ludmila [1 ]
机构
[1] Acad Sci Czech Republic, Inst Microbiol, Ctr Biocatalysis & Biotransformat, CZ-14220 Prague 4, Czech Republic
[2] Graz Univ Technol, Inst Organ Chem, A-8010 Graz, Austria
关键词
Amino nitriles; Nitrilase; Substrate specificity; Enantioselectivity; Diastereoselectivity; RHODOCOCCUS-RHODOCHROUS NCIMB-11216; ASYMMETRIC HYDROLYSIS; MILD HYDROLYSIS; PURIFICATION; ENZYME; BIOTRANSFORMATION; ACIDS;
D O I
10.1016/j.molcatb.2008.06.012
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The nitrilases from Fusarium solani O1 and Aspergillus niger K10 showed a broad substrate specificity for carbocyclic and nonaromatic heterocyclic amino nitriles, the preferred substrates being five-membered gamma-amino nitrile (+/-)-1a, six-membered gamma-amino nitriles (+/-)-3a, (+/-)-5a and (+/-)-6a, pyrrolidine-3-carbonitriles (+/-)-9a and (+/-)-10a as well as piperidine-4-carbonitriles 14a and 15a. Both enzymes showed a strong diastereopreference for cis- vs. trans-gamma-amino nitriles. The electronic and steric effects of N-protecting groups affected the reactivity of the nitriles. Amides as by-products of the nitrilase-catalyzed reaction were produced from heterocyclic amino nitriles (+/-)-9a, (+/-)-10a, 14a and 15a by the A. niger enzyme but only from nitrile (+/-)-9a by the F. solani enzyme. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:243 / 247
页数:5
相关论文
共 25 条
  • [1] Enzyme catalyzed reactions, part 40.: Enantioselective hydrolysis of (RS)-2-fluoroarylacetonitriles using nitrilase from Arabidopsis thaliana
    Effenberger, F
    Osswald, S
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (02) : 279 - 285
  • [2] Nitrile hydratase activity of a recombinant nitrilase
    Fernandes, Bruno C. M.
    Mateo, Cesar
    Kiziak, Christoph
    Chmura, Andrzej
    Wacker, Jan
    van Rantwijk, Fred
    Stolz, Andreas
    Sheldon, Roger A.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (18) : 2597 - 2603
  • [3] GOLDLUST A, 1989, BIOTECHNOL APPL BIOC, V11, P581
  • [4] GRADLEY ML, 1994, ARCH MICROBIOL, V161, P246, DOI 10.1007/s002030050049
  • [5] ASYMMETRIC HYDROLYSIS OF CHIRAL NITRILES BY RHODOCOCCUS-RHODOCHROUS NCIMB-11216 NITRILASE
    GRADLEY, ML
    KNOWLES, CJ
    [J]. BIOTECHNOLOGY LETTERS, 1994, 16 (01) : 41 - 46
  • [6] FUNGAL DEGRADATION OF AROMATIC NITRILES - ENZYMOLOGY OF C-N CLEAVAGE BY FUSARIUM-SOLANI
    HARPER, DB
    [J]. BIOCHEMICAL JOURNAL, 1977, 167 (03) : 685 - 692
  • [7] The nitrilases of Rhodococcus rhodochrous NCIMB 11216
    Hoyle, AJ
    Bunch, AW
    Knowles, CJ
    [J]. ENZYME AND MICROBIAL TECHNOLOGY, 1998, 23 (7-8) : 475 - 482
  • [8] Purification and characterization of a nitrilase from Aspergillus niger K10
    Kaplan, Ondrej
    Vejvoda, Vojtech
    Plihal, Ondrej
    Pompach, Petr
    Kavan, Daniel
    Bojarova, Pavla
    Bezouska, Karel
    Mackova, Martina
    Cantarella, Maria
    Jirku, Vladimir
    Kren, Vladimir
    Martinkova, Ludmila
    [J]. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2006, 73 (03) : 567 - 575
  • [9] Hyperinduction of nitrilases in filamentous fungi
    Kaplan, Ondrej
    Vejvoda, Vojtech
    Charvatova-Pisvejcova, Andrea
    Martinkova, Ludmila
    [J]. JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY, 2006, 33 (11) : 891 - 896
  • [10] Nitrilase from Pseudomonas fluorescens EBC191:: cloning and heterologous expression of the gene and biochemical characterization of the recombinant enzyme
    Kiziak, C
    Conradt, D
    Stolz, A
    Mattes, R
    Klein, J
    [J]. MICROBIOLOGY-SGM, 2005, 151 : 3639 - 3648