High-throughput method for determining the enantioselectivity of enzyme-catalyzed hydroxylations based on mass spectrometry

Angewandte Chemie - International Edition

Volumn 49, Issue 31, 2010, Pages 5278-5283

  Chen, Yongzheng ^a   Tang, Weng Lin ^a   Mou, Jie ^a   Li, Zhi ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Enantioselectivity; Enzyme catalysis; High throughput screening; Hydroxylation; Mass spectrometry

Indexed keywords

CHEMICAL EQUATIONS; ENANTIOPURE; ENZYME CATALYSIS; HIGH-THROUGHPUT; HIGH-THROUGHPUT METHOD; HIGH-THROUGHPUT SCREENING; MASS SPECTROMETRIC DETECTION; SIMPLE METHOD;

CATALYSIS; CHEMICAL DETECTION; DEUTERIUM; ELECTRON TRANSITIONS; ENZYMES; HYDROXYLATION; MASS SPECTROMETRY; THROUGHPUT;

ENANTIOSELECTIVITY;

MIXED FUNCTION OXIDASE;

ARTICLE; CATALYSIS; CHEMISTRY; HUMAN; HYDROXYLATION; KINETICS; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; PSEUDOMONAS; STEREOISOMERISM;

CATALYSIS; HUMANS; HYDROXYLATION; KINETICS; MASS SPECTROMETRY; MIXED FUNCTION OXYGENASES; PSEUDOMONAS; STEREOISOMERISM;

EID: 77954859964     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201001772     Document Type: Article

References (86)

1. a) J. Zhang, G. Lin in Drug Discovery Research (Ed. : Z. Huang), Wiley, 2007, pp. 230-280;
2. b) Chirality in Industry II: The Commercial Manufacture and Applications of Optically Active Compounds (Eds.: A.N. Collins, G.N. Sheldrake, J. Crosby), Wiley, Chichester, 1997, pp. 1-426.
3. For reviews, see: a) M. T. Reetz, Angew. Chem. 2008, 120, 2592-2626;
4. Angew. Chem. Int. Ed. 2008, 47, 2556-2588;
5. b) A. Berkessel, Curr. Opin. Chem. Biol. 2003, 7, 409-419;
6. c) J. P. Stambuli, J. F. Hartwig, Curr. Opin. Chem. Biol. 2003, 7, 420-426;
7. d) A. Hagemeyer, B. Jandeleit, Y. Liu, D. M. Poojary, H. W. Turner, A. F. Volpe, Jr., W. H. Weinberg, Appl. Catal A 2001, 221, 23-43;
8. e) K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Curr. Opin. Chem Biol. 1999, 3, 313-319.
9. For reviews, see: a) M. T. Reetz, K.-E. Jaeger, Chem. Eur. J. 2000, 6, 407-412;
10. b) K.-E. Jaeger, M. T. Reetz, Curr. Opin. Chem. Biol. 2000, 4, 68-73;
11. c) M. T. Reetz, Tetrahedron 2002, 58, 6595-6602;
12. d) M. T. Reetz, Adv. Catal. 2006, 49, 1-69;
13. e) M. T. Reetz, J. Org. Chem. 2009, 74, 5767-5778.
14. For examples, see: a) M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger, Angew. Chem. 1997, 109, 2961-2963;
15. Angew. Chem. Int. Ed. Engl. 1997, 36, 2830-2832;
16. b) M. T. Reetz, S. Wilensek, D. Zha, K.-E. Jaeger, Angew. Chem. 2001, 113, 3701-3703;
17. Angew. Chem. Int. Ed. 2001, 40, 3589-3591;
18. c) D. Zha, S. Wilensek, M. Hermes, K.-E. Jaeger, M. T. Reetz, Chem. Commun. 2001, 2664-2665;
19. d) E. Henke, T. Bornscheuer, Biol. Chem. 1999, 380, 1029-1033;
20. e) O. May, P. T. Nguyen, F. H. Arnold, Nat. Biotechnol 2000, 18, 317-320;
21. f) M. T. Reetz, Proc Natl. Acad. Sci. USA 2004, 101, 5716-5722;
22. g) M. T. Reetz, L.-W. Wang, M. Bocola, Angew. Chem. 2006, 118, 1258-1263;
23. Angew. Chem. Int. Ed. 2006, 45, 1236-1241.
24. a) E. T. Farinas, T. Bulter, F. H. Arnold, Curr. Opin. Biotechnol. 2001, 12, 545-551;
25. b) W. P. C. Stemmer, Proc. Natl. Acad. Sci. USA 1994, 91, 10747-10751;
26. c) W. P. C. Stemmer, Nature 1994, 370, 389-391.
27. For reviews, see: a) M. T. Reetz, Angew. Chem. 2001, 113, 292-320;
28. b) M. T. Reetz, Angew. Chem. 2002, 114, 1391-1394;
29. Angew. Chem. Int. Ed. 2002, 41, 1335-1338;
30. c) D. Wahler, J. L. Reymond, Curr. Opin. Biotechnol. 2001, 12, 535-544;
31. d) L. G. Otten, F. Hollmann, I. W. C. E. Arends, Trends Biotechnol .2010, 28, 46-54;
32. e) J. Goddard, J. L. Reymond, Curr. Opin. Biotechnol. 2004, 15, 314-322;
33. f) Q. Zhang, D. P. Curran, Chem. Eur. J. 2005, 11, 4866-4880;
34. g) C. A. Müller, C. Markert, A. M. Teichert, A. Pfaltz, Chem. Commun. 2009, 1607-1618.
35. a) C. A. Müller, A. Pfaltz, Angew. Chem. 2008, 120, 3411-3414;
36. b) A. Teichert, A. Pfaltz, Angew. Chem. 2008, 120, 3408-3410;
37. c) G. Klein, J.-L. Reymond, Helv. Chim. Acta 1999, 82, 400-407.
38. a) M. T. Reetz, K. M. Kuehling, S. Wilensek, H. Husmann, U. W. Hausig, M. Hermes, Catal. Today 2001, 67, 389-396;
39. b) K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519-523;
40. Angew. Chem. Int. Ed. 1999, 38, 497-501;
41. c) K. Mikami, R. Angelaud, K. Ding, A. Ishii, A. Tanaka, N. Sawada, K. Kudo, M. Senda, Chem. Eur. J. 2001, 7, 730-737;
42. d) M. T. Reetz, K. M. Kuehling, A. Deege, H. Hinrichs, D. Beider, Angew. Chem 2000, 112, 4049-4052;
43. Angew. Chem. Int. Ed. 2000, 39, 3891-3893;
44. e) W. A. Tao, R. G. Cooks, Angew. Chem. 2001, 113, 779-782;
45. f) R. A. van Delden, B. L. Feringa, Angew. Chem. 2001, 113, 3298-3300;
46. g) F. Taran, C. Gauchet, B. Mohar, S. Meunier, A. Valleix, P. Y. Renard, C. Creminon, J. Grassi, A. Wagner, C. Mioskowski, Angew. Chem. 2002, 114, 132 -135;
47. a) A. Schoofs, A. Horeau, Tetrahedron Lett. 1977, 18, 3259-3262;
48. b) J. Guo, J. Wu, G. Siuzdak, M. G. Finn, Angew. Chem. 1999, 111, 1868-1871;
49. c) S. Yao, J.-C. Meng, G. Siuzdak, M. G. Finn, J. Org. Chem. 2003, 68, 2540-2546;
50. d) G. A. Korbel, G. Lalic, M. D. Shair, J. Am. Chem. Soc. 2001, 123, 361-362.
51. a) P. Abato, C. T. Seto, J. Am. Chem. Soc. 2001, 123, 9206-9207;
52. b) N. Millot, P. Borman, M. S. Anson, I. B. Campbell, S. J. F. Macdonald, M. Mahmoudian, Org. Process Res. Dev. 2002, 6, 463-470.
53. Z. Li, L. Butikofer, B. Witholt, Angew. Chem. 2004, 116, 1730-1734;
54. Angew. Chem. Int. Ed. 2004, 43, 1698-1702.
55. a) J. T. Groves, P. Viski, J. Am. Chem. Soc. 1989, 111, 8537-8538;
56. b) G. Battaini, E. Monzani, A. Perotti, C. Para, L. Casella, L. Santagostini, M. Gullotti, R. Dillinger, C. Näther, F. Tuczek, J. Am. Chem. Soc. 2003, 125, 4185-4198.
57. For reviews, see: a) H. L. Holland, H. K. Weber, Curr. Opin. Biotechnol. 2000, 11, 547-553;
58. b) H. L. Holland, Steroids 1999, 64, 178-186;
59. c) Z. Li, J. B. Beilen, W. A. Duetz, A. Schmid, A. Raadt, H. Griengl, B. Witholt, Curr. Opin. Chem. Biol. 2002, 6, 136-144;
60. d) S. G. Burton, Trends Biotechnol. 2003, 21, 543-549.
61. a) D. Chang, B. Witholt, Z. Li, Org. Lett. 2000, 2, 3949-3952;
62. b) D. Chang, H. J. Feiten, K. H. Engesser, J. B. Beilen, B. Witholt, Z. Li, Org. Lett. 2002, 4, 1859-1862;
63. c) D. Chang, H. J. Feiten, B. Witholt, Z. Li, Tetrahedron: Asymmetry 2002, 13, 2141-2147;
64. d) Y. Chen, J. Xu, X. Xu, Y. Xia, H. Lin, S. Xia, L. Wang, Tetrahedron: Asymmetry 2007, 18, 2537-2540;
65. e) H. L. Holland, T. A. Morris, P. J. Nava, M. Zabic, Tetrahedron 1999, 55, 7441-7460;
66. f) R. Weis, M. Winkler, M. Schittmayer, S. Kambourakis, M. Vink, J. D. Rozzell, A. Glieder, Adv. Synth. Catal. 2009, 351, 2140-2146;
67. g) D.F. Münzer, P. Meinhold, M. W. Peters, S. Feichtenhofer, H. Griengl, F. H. Arnold, A. Glieder, A. Raadt, Chem. Commun. 2005, 2597-2599;
68. h) G. Braunegg, A. Raadt, S. Feichtenhofer, H. Griengl, I. Kopper, A. Lehmann, H. Weber, Angew. Chem. 1999, 111, 2946-2949;
69. i) A. Raadt, H. Griengl, H. J. Weber, Chem. Eur. J. 2001, 7, 27-31;
70. j) A. Raadt, H. Griengl, Curr. Opin. Biotechnol. 2002, 13, 537-542.
71. a) Z. Li, D. Chang, Curr. Org. Chem. 2004, 8, 1647-1658;
72. b) L. Wen, A. Fulco, J. Biol. Chem. 1987, 262, 6676-6682;
73. c) M. Kok, R. Oldenhuis, M. Linden, P. Raatjes, J. Kingma, P. Lelyveld, B. Witholt, J. Biol. Chem. 1989, 264, 5435-5441;
74. d) A. W. Munro, D. G. Leys, K. J. McLean, K. R. Marshall, T. W. B. Ost, S. Daff, C. S. Miles, S. K. Chapman, D. A. Lysek, C. C. Moser, C. C. Page, P. L. Dutton, Trends Biochem. Sci. 2002, 27, 250-257;
75. e) S. G. Bell, R. J. Sowden, L. L. Wong, Chem. Commun. 2001, 635-636.
76. a) M. Landwehr, L. Hochrein, C. R. Otey, A. Kasrayan, J. E. Bäckvall, F. H. Arnold, J. Am. Chem. Soc 2006, 128, 6058-6059;
77. b) T. Kubo, M. W. Peters, P. Meinhold, F. H. Arnold, Chem. Eur. J. 2006, 12, 1216-1220;
78. c) M. W. Peters, P. Meinhold, A. Glieder, F. H. Arnold, J. Am. Chem. Soc. 2003, 125, 13442-13450.
79. a) M. T. Reetz, M. H. Becker, H. W. Klein, D. Stockigt, Angew. Chem. 1999, 111, 1872-1875;
80. b) W. Schrader, A. Eipper, D. J. Pugh, M. T. Reetz, Can. J. Chem. 2002, 80, 626-632.
81. A. M. Egorov, J. Phys Org. Chem. 2006, 19, 664-675.
82. Y. Chen, F. Lie, Z. Li, Adv. Synth. Catal. 2009, 351, 2107-2112.
83. Z. Li, H. J. Feiten, D. Chang, W. A. Duetz, J. B. Beilen, B. Witholt, J. Org. Chem. 2001, 66, 8424-8430.
84. a) J. Beilen, J. Kingma, B. Witholt, Enzyme Microb. Technol. 1994, 16, 904-911;
85. b) E. J. McKenna, M. J. Coon, J. Biol Chem. 1970, 245, 3882-3889;
86. c) G. Eggink, R. G. Lageveen, B. Alterburg, B. Witholt, J. Biol. Chem. 1987, 262, 17712-17718.