Chemoenzymatic synthesis of glycolic acid

Advanced Synthesis and Catalysis

Volumn 349, Issue 8-9, 2007, Pages 1462-1474

  Panova, Anna ^a   Mersinger, Lawrence J ^a   Liu, Qiang ^a   Foo, Thomas ^a   Roe, D Christopher ^a   Spillan, William L ^a   Sigmund, Amy E ^a   Ben Bassat, Arie ^a   Winona Wagner, L ^a   O'Keefe, Daniel P ^a   Wu, Shijun ^a   Perrillo, Kelly L ^a   Payne, Mark S ^a   Breske, Stephen T ^a   Gallagher, F Glenn ^a   Dicosimo, Robert ^a  

^a DUPONT COMPANY   (United States)

Author keywords

Enzyme catalysis; Glycolic acid; Glycolonitrile; Nitrilases

Indexed keywords

EID: 34547210832     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700061     Document Type: Article

References (60)

1. a) R. Datta, in: Kirk-Othmer Encycl. Chem. Technol., 5th edn., Vol. 14, (Ed.: A. Seidel), Wiley, Hoboken, NJ, 2005, pp 114-134;
2. b) E. Lower, Speciality Chemicals 1996, 16, 54-55;
3. c) E. Lower, Speciality Chemicals 1996, 16, 104-107.
4. Y. Yamamoto, K. Uede, N. Yonei, A. Kishioka, T. Ohtani, F. Furukawa, J. Dermatology 2006, 33, 16-22.
5. M. J. Hayes, M. D. Lauren, J. Appl. Biomat. 1994, 5, 215-220.
6. a) S. Shawe, F. Buchanan, E. Harkin-Jones, D. Farrar, J. Mater. Sci. 2006, 41, 4832-4838;
7. b) J.-H. Park, M. G. Allen, M. R. Prausnitz, J. Controlled Release 2005, 104, 51-66.
8. M. Wada, D. Mochizuki, H. Takahashi, T. Morishige, K. Takahashi, (Mitsui Chemicals Inc., Japan), PCT Int. Appl. WO 2005106005 A1, 2005;
9. Chem. Abstr. 2005, 143, 420969.
10. a) M. T. Shattuck, (E. I. du Pont de Nemours and Co., USA), US Patent 2,443,482, 1948;
11. Chem. Abstr. 1948, 42, 34349;
12. b) R. DiCosimo, (E. I. du Pont de Nemours and Co., USA), PCT Int. Appl. WO 9205138 A1, 1992;
13. Chem. Abstr. 1992, 117, 89843.
14. a) P. Cristol, C. Benezech, L. Merzer, Bull. Soc. Chim. 1944, 11, 58-63;
15. b) L. F. Berhenke, E. C. Britton, J. Ind. Eng. Chem. (Washington, D.C.) 1946, 38, 544-546.
16. Y. Chen, J. Zhang, W. Qin, (Taicang Xinyue Chemical Industry Co., Ltd., Peop. Rep. China), Faming Zhuanli Shenqing Gongkai Shuomingshu CN 1724504A, 2006;
17. Chem. Abstr. 2006, 144, 469985.
18. T. Nakamura, (Nitto Chemical Industry Co Ltd, Japan), Jpn. Kokai Tokkyo Koho JP 09028390A2, 1997;
19. Chem. Abstr. 1997, 126, 224356.
20. a) R. DiCosimo, T. Foo, M. S. Payne, A. Panova, D. P. O'Keefe, J. S. Thompson, F. G. Gallagher, X. Li, (E. I. Dupont de Nemours and Company, USA), PCT Int. Appl. WO 2006069114 A2, 2006;
21. Chem. Abstr. 2006, 145, 82085;
22. b) S. Chauhan, R. DiCosimo, R. D. Fallon, J. E. Gavagan, M. S. Payne, (E. I. Dupont de Nemours and Company, USA), US Patent 6,416,980 B1, 2002;
23. Chem. Abstr. 2002, 137, 78014.
24. J. Xue, J. Luo, H. Li, J. Yu, J. Zhu, H. Xu, Y. Shen, (Shanghai Pesticide Research Institute, Peop. Rep. China), Faming Zhuanli Shenqing Gongkai Shuomingshu CN 1772912 A, 2006;
25. Chem. Abstr. 2006, 145, 102249.
26. H. Hinago, H. Nagahara, T. Aoki, (Asahi Kasei Chemicals Corporation, Japan), PCT Int. Appl. WO 2006126626 A1 2006;
27. Chem. Abstr. 2006, 146, 8423.
28. A. Dalal, ; K. Furuya, A. Tamaki, (Asahi Kasei Corporation, Japan), Jpn. Kokai Tokkyo Koho JP 2006067823 A, 2006;
29. Chem. Abstr. 2006, 144, 252811.
30. A. Dalal, ; K. Furuya, A. Tamaki, (Asahi Kasei Corporation, Japan), Jpn. Kokai Tokkyo Koho JP 2006067822 A, 2006;
31. Chem. Abstr. 2006, 144, 252810.
32. a) R. A. Jacobson, (E. I. du Pont de Nemours & Co.), US Patent 2,175,805, 1939;
33. Chem. Abstr. 1940, 34, 4757;
34. b) A. R. Sexton, (Dow Chemical Co.), US Patent 2,890,238, 1959;
35. Chem. Abstr. 1959, 53, 111328;
36. c) B. A. Cullen, B. A. Parker, (W. R. Grace and Co.), US Patent 5,187,301, 1993;
37. Chem. Abstr. 1991, 115, 91679.
38. G. Schlesinger, S. L. Miller, J. Am. Chem. Soc. 1973, 95, 3729-3735.
39. T. Grützner, H. Hasse, J. Chem. Eng. Data 2004, 49, 642-646.
40. J. F. Walker, Formaldehyde, 3rd edn., Reinhold, New York, 1964.
41. T. Ihara, M. Sasaki, H. Myauchi, (Mitsubishi Chemical Industries Co., Ltd., Japan), Jpn. Kokai Tokkyo Koho JP 06135923 A, 1994;
42. Chem. Abstr. 1994, 121, 280263.
43. D. B. Lake, T. E. Londergan, J. Org. Chem. 1954, 19, 2004-2007.
44. S. Chauhan, S. Wu, S. Blumerman, R. D. Fallon, J. E. Gavagan, R. DiCosimo, M. S. Payne, Appl. Microbiol. Biotechnol. 2003, 61, 118-122.
45. a) S. Wu, A. J. Fogiel, K. L. Petrillo, E. C. Hann, L. J. Mersinger, R. DiCosimo, D. P. O'Keefe, A. Ben-Bassat, M. S. Payne, Biotechnol. Bioengin. 2007, in press;
46. b) M. S. Payne, manuscript in preparation.
47. a) L. J. Mersinger, E. C. Hann, F. B. Cooling, A. Ben-Bassat, J. E. Gavagan, S. Wu, K. L. Petrillo, M. S. Payne, R. DiCosimo, Adv. Synth. Catal. 2005, 347, 1125-1131;
48. b) E. C. Hann, A. E. Sigmund, S. K. Fager, F. B. Cooling, J. E. Gavagan, A. Ben-Bassat, S. Chauhan, M. S. Payne, S. M. Hennessey, R. DiCosimo, Adv. Synth. Catal. 2003, 345, 775-782;
49. F. B. Cooling, S. K. Fager, R. D. Fallon, P. W. Folsom, F. G. Gallagher, J. E. Gavagan, E. Hann, F. E. Herkes, R. L. Phillips, A. Sigmund, L. W. Wagner, W. Wu, R. DiCosimo, J. Mol. Catal. B: Enzymatic 2001, 11, 295-306.
50. G. Arrhenius, K. K. Baldridge, S. Richards-Gross, J. S. Siegel, J. Org. Chem. 1997, 62, 5522-5525.
51. B. Atkinson, F. Mavituna, Biochemical Engineering and Biotechnology Handbook, 2nd edn., MacMillan, New York, 1991, pp 638-645.
52. B. A. Orsi, K. F. Tipton, Meth. Enzymol. 1979, 63, 159-183.
53. a) R. DiCosimo, in: Biocatalysis in the Pharmaceutical and Biotechnology Industries, (Ed.: R. N. Patel), CRC Press, New York, 2006, pp 1-26;
54. b) C. O'Reilly, P. D. Turner, J. Appl. Microbiol. 2003, 95, 1161-1174;
55. c) L. Martinkova, V. Mylerova, Curr. Org. Chem. 2003, 7, 1279-1295;
56. d) L. Martinkova, V. Kren, Biocatal. Biotransform. 2002, 20, 73-93;
57. e) A. Banerjee, R. Sharma, U. C. Banerjee, Appl. Microbiol. Biotechnol. 2002, 60, 33-44;
58. f) C. Brenner, Curr. Opin. Struct. Biol. 2002, 12, 775-782;
59. g) H. Groger, Adv. Synth. Catal. 2001, 343, 547-558;
60. h) M. Wieser, T. Nagasawa, in: Stereoselective Biocatalysis, (Ed.; R. N. Patel), Marcel Dekker, New York, 2000, pp 461-486.