Bioconversion of D,L-tert-leucine nitrile to D-tert-leucine by recombinant cells expressing nitrile hydratase and D-selective amidase

Engineering in Life Sciences

Volumn 4, Issue 6, 2004, Pages 547-556

  Brandão, Pedro F B ^b,c   Verseck, Stefan ^a   Syldatk, Christoph ^b,c  

^a Project House ProFerm   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

^c UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCONVERSION; CELLS; CHEMICAL REACTORS; ESCHERICHIA COLI; NITROGEN COMPOUNDS; STRAIN; THERMAL EFFECTS;

BACTERIAL STRAIN; BIOTRANSFORMATIONS; NITRILE HYDRATASES; RACEMIC AMIDES;

ENZYMES;

AMIDASE; LEUCINE; NITRILE; NITRILE HYDRATASE;

BIOTRANSFORMATION; COLIFORM BACTERIUM; ENZYME;

ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; BIOTRANSFORMATION; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME MECHANISM; ESCHERICHIA COLI; NONHUMAN; RACEMIC MIXTURE; RHODOCOCCUS ERYTHROPOLIS;

BACTERIA (MICROORGANISMS); RHODOCOCCUS; RHODOCOCCUS ERYTHROPOLIS; VARIOVORAX PARADOXUS;

EID: 11144267375     PISSN: 16180240     EISSN: None     Source Type: Journal    
DOI: 10.1002/elsc.200402153     Document Type: Article

References (30)

1. Y. Asano, T L. Lübbehüsen, Enzymes acting on peptides containing D-amino acid, J. Biosci. Bioeng. 2000, 89, 295.
2. A. Bruggink, E. C. Roos, E de Vroom, Penicillin acylase in the industrial production of β-lactam antibiotics, Org. Process Res. Dev. 1998, 2, 128.
3. L. A. Thompson, C. J. Knowles, E. A. Linton, J. M. Wyatt, Microbial biotransformations of nitriles, Chem. Br. 1988, 900.
4. T. Nagasawa, H. Yamada, Microbial transformations of nitriles, Trends Biotechnol. 1989, 7, 153.
5. A. Banerjee, R. Sharma U. C. Banerjee, The nitrile-degrading enzymes: current status and future prospects, Appl. Micobiol. Biotechnol. 2002, 60, 33.
6. A. S. Bommarius, M. Schwarm, K. Drauz, Biocatalysis to amino acid-based chiral pharmaceuticals - examples and perspectives, J. Mol. Catal. B: Enzym. 1998, 5, 1.
7. A. S. Bommarius, M. Schwarm, K. Stingl, M. Kottenhahn, K. Huthmacher, K. Drauz, Synthesis and use of enantiomerically pure tert-leucine, Tetrahedron: Assymetry 1995, 6, 2851.
8. M. S. Sigman, P. Vachal, E. N. Jacobsen, A general catalyst for the asymmetric Strecker reaction, Angew. Chem. Int. Ed. 2000 39, 1279.
9. P. F. B. Brandão, J. P. Clapp, A. T. Bull, Discrimination and taxonomy of geographically diverse strains of nitrile-metabolising actinomycetes using chemometric and molecular sequencing techniques, Environ. Microbiol. 2002, 4, 262.
10. P. F. B. Brandão, J. P. Clapp, A. T. Bull, Diversity of nitrile hydratase and amidase enzyme genes in Rhodococcus erythropolis recovered from geographically distinct habitats, Appl. Environ. Microbiol. 2003, 69, 5754.
11. L. Krieg, M. B. Ansorge-Schumacher, M. R. Kula, Screening for amidases: isolation and characterization of D-amidase from Variovorax paradoxus, Adv. Synth. Catal. 2002, 344, 965.
12. P. F. B. Brandão, A. T. Bull, Nitrile hydrolysing activities of deep-sea and terrestrial mycolate actinomycetes, Antonie van Leeuwenhoek 2003, 84, 89.
13. I. Osprian, C. Jarret, U. Strauss, W. Kroutil et al., Large-scale preparation of a nitrile hydrolysing biocatalyst: Rhodococcus R312 (CBS 717.73), J. Mol. Catal. B: Enzym. 1999 6, 555.
14. S. C. Heald, P. F. B Brandão, R. Hardicre, A. T. Bull, Physiology, biochemistry and taxonomy of deep-sea nitrile metabolising Rhodococcus strains, Antonie van Leeuwenhoek 2001, 80 169.
15. W.-Y. Phong, S. Verseck, unpublished.
16. T. Stumpp, B. Wilms, J. Altenbuchner, A new L-rhamnose-inducible expression system for Escherichia coli, BIOspektrum 2000, 6, 33.
17. B. Vennesland, E. E. Conn, C. J. Knowles, J. Westley, F. Wissiing, Cyanide in Biology, Academic Press, London 1981.
18. K. Bui, M. Maestracci, A. Thiery, A. Arnaud, P. Galzy, A note on the enzymatic action and biosynthesis of a nitrile-hydratase from a Brevibacterium sp., J. Appl. Bacteriol. 1984, 57, 183.
19. T. Amarant, Y. Vered, Z. Bohak, Substrates and inhibitors of the Nitrile hydratase and amidase of Corynebacterium nitrilophilus, Biotechnol. Appl. Biochem. 1989, 11, 49.
20. J. C. Jallageas, H. Fradet, K. Bui, M. Maestracci et al., Development of an assay method for cyanide, α-aminonitriles and α-hydroxynitriles for the study of the biological hydrolysis of these compounds, Analyst 1984, 109, 1439.
21. K. Kawashiro, S. Morimoto, H. Yoshida, K. Sugiura, The synthesis and chromatography of peptine nitriles, Orig. Life 1977, 8, 347.
22. A. L. L. Duchateau, M. G. Crombach, Determination of α-aminonitriles, α-amino acids amides and α-amino acids by means of HPLC, post-column reaction and fluorescence detection, Chromatographia 1987, 24, 339.
23. M. A. Wegman, U. Heinemann, A. Stolz, F. van Rantwijk, R. A. Sheldon, Stereoretentive nitrile hydratase-catalysed hydration of D-phenylglycine nitrile, Org. Process Res. Dev. 2000, 4 318.
24. D. A. Cowan, R. A. Cameron, T. L. Tsekoa, Comparative biology of mesophilic and thermophilic nitrile hydratases, Adv. Appl. Microbiol. 2003, 52, 123.
25. K. Faber, Biotransformations in Organic Chemistry, Springer, Berlin 1992.
26. L. A. Martínková, A. Stolz, H. J. Knackmuss, Enateoselectivity of the nitrile-hydratase from Rhodococcus equi A4 towards substituted (R,S)-2-arylpropionitriles, Biotechnol. Lett. 1996, 18, 1073.
27. L. A. Martínková, V. Kren, Nitrile- and amide-converting microbial enzymes: stereo-, regio- and chemoselectivity, Biocatal. Biotransform. 2002, 20, 73.
28. T. Hongpattarakere, N. Seksun, A. Suriya, Isolation and screening of D-amino acid amidase producing bacteria from soil samples, J. Sci. Technol. 2003, 25, 255.
29. A. Rosevear, J. F. Kennedy, J. M. S. Cabral, Immobilised Enzymes and Cells, Adam Hilger - IOP Publishing, Bristol 1987.
30. T. Endo, T Doi, K. Tamura, Y. Hirata, K. Murao, US Patent 5 705 382, 1998.