Biocatalytic Hydrolysis of 3-Hydroxyalkanenitriles to 3-Hydroxyalkanoic Acids

Advanced Synthesis and Catalysis

Volumn 345, Issue 6-7, 2003, Pages 775-782

  Hann, Eugenia C ^a   Sigmund, Amy E ^a   Fager, Susan K ^a   Cooling, Frederick B ^a   Gavagan, John E ^a   Ben Bassat, Arie ^a   Chauhan, Sarita ^a   Payne, Mark S ^a   Hennessey, Susan M ^a   DiCosimo, Robert ^a  

^a DUPONT COMPANY   (United States)

Author keywords

3 hydroxyal; 3 hydroxyalkanoic acid; Amidase; Enzyme catalysis; Kanenitrile; Nitrilase; Nitrile hydratase

Indexed keywords

ALGINIC ACID; ALKANE DERIVATIVE; AMIDASE; AMMONIUM DERIVATIVE; MICROBIAL ENZYME; NITRILASE; NITRILE; NITRILE HYDRATASE; VALERIC ACID DERIVATIVE;

ARTICLE; BIOCATALYST; CATALYSIS; COMAMONAS TESTOSTERONI; ENZYME ACTIVITY; ENZYME IMMOBILIZATION; ENZYME MECHANISM; ENZYME STABILITY; HYDROLYSIS; QUANTUM YIELD; REACTION ANALYSIS;

EID: 0242691648     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303007     Document Type: Article

References (43)

1. I. Goodman, in Concise Encyclopedia of Polymer Science and Engineering, (Ed.: J. I. Kroschwitz), John Wiley & Sons, New York, 1990, pp. 793-799.
2. J. Hasegawa, N. Nagashima, in Stereoselective Biocatalysis, (Ed.: R. N. Patel), Marcel Dekker, New York, 2000, pp. 343-363.
3. J. Hasegawa, S. Hamaguchi, M. Ogura, K. Watanabe, J. Ferment. Technol. 1981, 59, 257-262.
4. C. T. Goodhue, J. R. Schaeffer, (Eastman Kodak Company), US Patent 3,553,081, 1971; Chem. Abstr. 1970, 1970, 475675.
5. D. Seebach, T. Hoffmann, F. N. M. Kuhnle, U. D. Lengweiler, Helv. Chim. Acta 1994, 77, 2007-2034.
6. S. Y. Lee, F. Wang, Y. Lee, (LG Chemical Ltd., S. Korea), PCT Int. Appl. WO9929889 A1, 1999; Chem. Abstr. 1999, 131, 43677.
7. M. J. Burk, J. E. Feaster, R. L. Harlow, Organometallics 1990, 9, 2653-2655.
8. a) M. Bayer, M. Schulz, H. Gunther, H. Simon, Appl. Microbiol. Biotechnol. 1994, 42, 543-547;
9. b) M. Utaka, H. Watabu, H. Higashi, T. Sakai, S. Tsuboi, S. Torii, J. Org. Chem. 1990, 55, 3917-3921.
10. R. R. Gokarn, O. V. Selifonova, H. Jessen, S. J. Gort, T. Selmer, W. Buckel, (Cargill, Incorporated, USA), PCT Int. Appl. WO0242418 A2, 2002; Chem. Abstr. 2002, 137, 1501.
11. a) W. Umbach, R. Mehren, W. Stein, (Henkel & Cie, GmbH), US Patent 3,862,204, 1975; Chem. Abstr. 1971, 74, 3330;
12. b) H. Hamana, T. Sugasawa, Chem. Lett. 1982, 1401 -1404;
13. c) K. G. Golodova, S. I. Yakimovich, Journal of Organic Chemistry (USSR) 1972, 8, 2530-2536;
14. d) F. E. Herkes, (E. I. du Pont de Nemours and Company), US Patent Appl. 20020022737 A1, 2002; Chem. Abstr. 2002, 136, 183534.
15. a) J. H. Ford, Org. Synth. 1955, Coll. Vol. III, 34-36;
16. b) G. B. Brown, Org Synth. 1955, Coll. Vol. III, 615-617.
17. a) L. Martinkova, V. Kren, Biocatalysis and Biotransformation 2002, 20, 73-93;
18. b) B. Schulze, in Enzyme Catalysis in Organic Synthesis, 2nd Edn., (Eds.: K. Drauz, H. Waldman), Wiley-VCH, Weinheim, 2002, Vol. 2, pp. 699-715;
19. c) M. Kobayashi, S. Shimizu, Curr. Opinion Chem. Biol. 2000, 4, 95-102.
20. a) D. Cowan, R. Cramp, R. Pereira, D. Graham, Q. Almatawah, Extremophiles 1998, 2, 207-216;
21. b) T. Sugai, T. Yamazaki, M. Yokoyama, H. Ohta, Biosci. Biotech. Biochem. 1997, 61, 1419-1427.
22. A. de Raadt, N. Klempier, K. Faber, H. Griengl, J. Chem. Soc. Perkin Trans. 1 1992, 137-140.
23. R. Cramp, D. A. Cowan, Biochim. Biophys. Acta 1999, 1431, 249-260.
24. G. DeSantis, Z. Zhu, W. A. Greenberg, K. Wong, J. Chaplin, S. R. Hanson, B. Farwell, L. W. Nicholson, C. L. Rand, D. P. Weiner, D. E. Robertson, M. J. Burk, J. Am. Chem. Soc. 2002, 124, 9024-9025.
25. S. Chauhan, S. Wu, S. Blumeman, R. D. Fallon, J. E. Gavagan, R. DiCosimo, M. S. Payne, Appl. Microbiol. Biotechnol. 2003, 67, 118-122.
26. a) D. B. Harper, Biochem. Soc. Trans. 1976, 4, 502-504;
27. b) C. Bengis-Garber, A. L. Gutman, Appl. Microbiol. Biotechnol. 1989, 32, 11-16;
28. c) M. L. Gradley, C. Knowles, Biotechnol. Lett. 1994, 16, 41-46.
29. a) D. E. Stevenson, R. Feng, F. Dumas, D. Groleau, A. Mihoc, A. C. Storer, Biotechnol. Appl. Biochem. 1992, 15, 283-302;
30. b) W. D. Prevatt, C. Akin, A. J. Evans, (Standard Oil Company, Indiana), US Patent 4,629,700, 1986; Chem. Abstr. 1970, 106, 100879.
31. a) E. C. Hann, A. E. Sigmund, S. M. Hennessey, J. E. Gavagan, D. R. Short, A. Ben-Bassat, S. Chauhan, R. D. Fallon, M. S. Payne, R. DiCosimo, Org. Proc. Res. Dev. 2002, 6, 492-496;
32. b) J. E. Gavagan, S. K. Fager, P. W. Folsom, A. Eisenberg, E. C. Hann, R. DiCosimo, K. Schneider, R. D. Fallon, Appl. Microbiol. Biotechnol. 1999, 52, 654-659.
33. M. G. Bramucci, R. Dicosimo, R. D. Fallon, J. E. Gavagan, F. E. Herkes, L. Wilczek, (E. I. du Pont de Nemours and Company), US Patent Appl. 20020039770 A1, 2002; Chem. Abstr. 2002, 136, 182562].
34. J. E. Gavagan, S. K. Fager, R. D. Fallon, P. W. Folsom, F. E. Herkes, A. Eisenberg, E. C. Hann, R. DiCosimo, J. Org. Chem. 1998, 63, 4792-4801.
35. E. C. Hann, A. E. Sigmund, S. M. Hennessey, J. E. Gavagan, D. R. Short, A. Ben-Bassat, S. Chauhan, R. D. Fallon, M. S. Payne, R. DiCosimo, Org. Proc. Res. Dev. 2002, 6, 492-496.
36. a) H. Brandenberger, F. Widmer, J. Biotechnol. 1998, 63, 73-80;
37. b) J. C. Ogbonna, M. Matsumura, T. Yamagata, H. Sakuma, H. Kalaoka J. Ferm. Bioeng. 1989, 68, 40-48.
38. P. Breuilles, R. Leclerc, D. Uguen, Tetrahedron Lett. 1994, 35, 1401-1404.
39. A. Adickes, Justus Liebigs Ann. Chem. 1944, 555, 46-56.
40. J. K. Fawcett, J. E. Scott, J. Clin. Pathol. 1960, 13, 156-159.
41. B. A. Orsi, K. F. Tiplon, Meth. Enzymol. 1979, 63, 159-183.
42. N. Bernet, A. Arnaud, P. Galzy, Biocatalysis 1990, 3, 259-267.
43. D. Briand, E. Dubreucq, V. Perrier, J. Grimaud, P. Galzy, Microbios 1994, 78, 205-214.