Altering the regioselectivity of cytochrome P450 BM-3 by saturation mutagenesis for the biosynthesis of indirubin

Journal of Molecular Catalysis B: Enzymatic

Volumn 67, Issue 1-2, 2010, Pages 29-35

  Hu, Sheng ^a   Huang, Jun ^b   Mei, Lehe ^a   Yu, Qing ^a   Yao, Shanjing ^a   Jin, Zhihua ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Cytochrome P450 BM 3; Indirubin; Regioselectivity; Saturation mutagenesis

Indexed keywords

ANTI-CANCER AGENTS; CHRONIC MYELOGENOUS LEUKEMIA; CYTOCHROME P450 BM3; DOCKING CALCULATIONS; HEME IRON; HIGH-PURITY; INDIRUBIN; PRODUCT YIELDS; PROTEIN ENGINEERING; PYRROLE RING; SATURATION MUTAGENESIS;

BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; BIOSYNTHESIS; ENZYMES; GENETIC ENGINEERING; HYDROXYLATION; MUTAGENESIS; PORPHYRINS;

REGIOSELECTIVITY;

ANTINEOPLASTIC AGENT; CYTOCHROME P450 BM3; INDIRUBIN; INDOLE; NONHEME IRON PROTEIN; OXYGENASE; PYRROLE; TOLUENE ORTHO MONOOXYGENASE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYST; BIOSYNTHESIS; CATALYSIS; CHRONIC MYELOID LEUKEMIA; ENZYME ACTIVITY; ENZYME ENGINEERING; ENZYME MECHANISM; ENZYME SYNTHESIS; HYDROXYLATION; MOLECULAR DOCKING; SITE DIRECTED MUTAGENESIS; STEREOCHEMISTRY;

EID: 77956928315     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcatb.2010.07.001     Document Type: Article

References (66)

1. U.T. Bornscheuer, and M. Pohl Curr. Opin. Chem. Biol. 5 2001 137 143
2. P.C. Cirino, and F.H. Arnold Curr. Opin. Chem. Biol. 6 2002 130 135
3. V.B. Urlacher, and R.D. Schmid Curr. Opin. Chem. Biol. 10 2006 156 161
4. K.L. Tee, and U. Schwaneberg Comb. Chem. High Throughput Screen. 10 2007 197 217
5. Z. Li, J.B. van Beilen, W.A. Duetz, A. Schmid, A. de Raadt, H. Griengl, and B. Witholt Curr. Opin. Chem. Biol. 6 2002 136 144
6. J.B. van Beilen, W.A. Duetz, A. Schmid, and B. Witholt Trends Biotechnol. 21 2003 170 177
7. B. Schulze, and M.G. Wubbolts Curr. Opin. Biotechnol. 10 1999 609 615
8. M. Dietrich, T.A. Do, R.D. Schmid, J. Pleiss, and V.B. Urlacher J. Biotechnol. 139 2009 115 117
9. 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, and P.L. Dutton Trends Biochem. Sci. 27 2002 250 257
10. H.M. Girvan, T.N. Waltham, R. Neeli, H.F. Collins, K.J. McLean, N.S. Scrutton, D. Leys, and A.W. Munro Biochem. Soc. Trans. 34 2006 1173 1177
11. S. Pug, S.M. Richter, and V.B. Urlacher J. Biotechnol. 129 2007 481 488
12. U. Schwaneberg, A. Sprauer, C. Schmidt-Dannert, and R.D. Schmid J. Chromatogr. A 848 1999 149 159
13. C.F. Oliver, S. Modi, M.J. Sutcliffe, W.U. Primrose, L.Y. Lian, and G.C.K. Roberts Biochemistry 36 1997 1567 1572
14. S. Graham-Lorence, G. Truan, J.A. Peterson, J.R. Falck, S.Z. Wei, C. Helvig, and J.H. Capdevila J. Biol. Chem. 272 1997 1127 1135
15. H. Joo, Z.L. Lin, and F.H. Arnold Nature 399 1999 670 673
16. O. Lentz, Q.S. Li, U. Schwaneberg, S. Lutz-Wahl, P. Fischer, and R.D. Schmid J. Mol. Catal. B: Enzym. 15 2001 123 133
17. P.C. Cirino, and F.H. Arnold Adv. Synth. Catal. 344 2002 932 937
18. M.W. Peters, P. Meinhold, A. Glieder, and F.H. Arnold J. Am. Chem. Soc. 125 2003 13442 13450
19. P. Meinhold, M.W. Peters, A. Hartwick, A.R. Hernandez, and F.H. Arnold Adv. Synth. Catal. 348 2006 763 772
20. C.J.C. Whitehouse, S.G. Bell, H.G. Tufton, R.J.P. Kenny, L.C.I. Ogilvie, and L.L. Wong Chem. Commun. 2008 966 968
21. R. Hoessel, S. Leclerc, J.A. Endicott, M.E.M. Nobel, A. Lawrie, P. Tunnah, M. Leost, E. Damiens, D. Marie, D. Marko, E. Niederberger, W.C. Tang, G. Eisenbrand, and L. Meijer Nat. Cell Biol. 1 1999 60 67
22. J. Ribas, X. Garrofé-Ochoa, J. Boix, in: L. Meijer, N. Guyard, L.A. Skaltsounis, G. Eisenbrand (Eds.), Indirubin, the Red Shade of Indigo, Editions "Life in Progress", Roscoff, 2006, pp. 215-226.
23. L. Meijer, J. Shearer, K. Bettayeb, Y. Ferandin, in: L. Meijer, N. Guyard, L.A. Skaltsounis, G. Eisenbrand (Eds.), Indirubin, the Red Shade of Indigo, Editions "Life in Progress", Roscoff, 2006, pp. 235-246.
24. C.H. Yu, Q.F. Wu, Z.H. Sheng, X.Y. Zeng, and D.H. Liu Zhong Yao Cai 29 2006 721 723
25. L.H. Cheng Zhong Yao Cai 30 2007 50 52
26. P. Aobchey, S. Sinchaikul, S. Phutrakul, and S.T. Chen Chiang Mai J. Sci. 34 2007 329 337
27. A. Baeyer Ber. Dtsch. Chem. Ges. 11 1878 1296 1297
28. G.W. Bae, C.S. Chung, K.I. Kim, C.H. Park, H.J. Lee, Y.A. Chae, and I.S. Chung Biotechnol. Technol. 12 1998 843 845
29. L.M. Marero, J.H. Jin, J.H. Shin, H.J. Lee, and I.S. Chung Enzyme Microb. Technol. 21 1997 97 101
30. S.U. Kim, K.S. Song, D.S. Jung, Y.A. Chae, and H.J. Lee Planta Med. 62 1996 54 56
31. I.S. Chung, T. Kim, G.W. Bae, H.J. Lee, and Y.A. Chae Biotechnol. Lett. 18 1996 947 950
32. S. Hart, K.R. Koch, and D.R. Woods J. Gen. Microbiol. 138 1992 211 216
33. E.M.J. Gillam, A.M.A. Aguinaldo, L.M. Notley, D. Kim, R.G. Mundkowski, A.A. Volkov, F.H. Arnold, P. Souek, J.J. DeVoss, and F.P. Guengerich Biochem. Biophys. Res. Commun. 265 1999 469 472
34. B. Bhushan, S.K. Samanta, and R.K. Jain Lett. Appl. Microbiol. 31 2000 5 9
35. H. Bialy Nat. Biotechnol. 15 1997 110 1110
36. T. Maugard, E. Enaud, P. Choisy, and M.D. Legoy Phytochemistry 58 2001 897 904
37. A. Berry, T. Dodge, M. Pepsin, and W. Weyler J. Ind. Microbiol. Biotechnol. 28 2002 127 133
38. L.Y. Rui, K.F. Reardon, and T.K. Wood Appl. Microbiol. Biotechnol. 66 2005 422 429
39. K. McClay, C. Boss, I. Keresztes, and R.J. Steffan Appl. Environ. Microbiol. 71 2005 5476 5483
40. E.M.J. Gillam, L.M. Notley, H.L. Cai, J.J. De Voss, and F.P. Guengerich Biochemistry 39 2000 13817 13824
41. Q.S. Li, U. Schwaneberg, P. Fischer, and R.D. Schmid Chem. Eur. J. 6 2000 1531 1536
42. H.K. Lim, E.J. Chung, J.C. Kim, G.J. Choi, K.S. Jang, Y.R. Chung, K.Y. Cho, and S.W. Lee Appl. Environ. Microbiol. 71 2005 7768 7777
43. H.M. Li, L.H. Mei, V.B. Urlacher, and R.D. Schmid Appl. Biochem. Biotechnol. 144 2008 27 36
44. R. Georgescu, G. Bandara, and L.H. Sun F.H. Arnold, G. Georgiou, Directed Evolution Library Creation: Methods and Protocols 2003 Humana Press Inc. Totowa 75 84
45. J. Sambrook, and D.W. Russell Molecular Cloning: A Laboratory Manual third ed. 2001 Cold Spring Harbor Laboratory Press New York
46. T. Omura, and R. Sato J. Biol. Chem. 239 1964 2370 2378
47. J. Ziegenhorn, M. Senn, and T. Bucher Clin. Chem. 22 1976 151 160
48. N. Guex, and M.C. Peitsch Electrophoresis 18 1997 2714 2723
49. J.J. Irwin, and B.K. Shoichet J. Chem. Inf. Model. 45 2005 177 182
50. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin J. Comput. Chem. 25 2004 1605 1612
51. L.Y. Rui, Y.M. Kwon, A. Fishman, K.F. Reardon, and T.K. Wood Appl. Environ. Microbiol. 70 2004 3246 3252
52. B.D. Ensley, B.J. Ratzkin, T.D. Osslund, M.J. Simon, L.P. Wackett, and D.T. Gibson Science 222 1983 167 169
53. J.M. Wang, W. Wang, P.A. Kollman, and D.A. Case J. Mol. Graph. Model. 25 2006 247 260
54. R.J. Sundberg Indoles first ed. 1996 Academic Press London
55. E. Notomista, V. Cafaro, G. Bozza, and A. Di Donato Appl. Environ. Microbiol. 75 2009 823 836
56. K.W. Choi, K.M. Park, S.Y. Jun, C.S. Park, K.H. Park, and J. Cha J. Microbiol. Biotechnol. 18 2008 901 907
57. A. Fishman, Y. Tao, L.Y. Rui, and T.K. Wood J. Biol. Chem. 280 2005 506 514
58. M. Dion, G. Osanjo, C. André, P. Spangenberg, C. Rabiller, and C. Tellier Glycoconj. J. 18 2001 457 464
59. M.G. Joyce, H.M. Girvan, A.W. Munro, and D. Leys J. Biol. Chem. 279 2004 23287 23293
60. S.A. Maves, H. Yeom, M.A. McLean, and S.G. Sligar FEBS Lett. 414 1997 213 218
61. S.K. Padhi, D.J. Bougioukou, and J.D. Stewart J. Am. Chem. Soc. 131 2009 3271 3280
62. C.L. Yu, R.E. Parales, and D.T. Gibson J. Ind. Microbiol. Biotechnol. 27 2001 94 103
63. H. Suenaga, T. Watanabe, M. Sato, K. Ngadiman, and Furukawa J. Bacteriol. 184 2002 3682 3688
64. K. Pollmann, V. Wray, H.J. Hecht, and D.H. Pieper Microbiology 149 2003 903 913
65. D.A. Rock, A.E. Boitano, J.L. Wahlstrom, and J.P. Jones Bioorg. Chem. 30 2002 107 118
66. N.R. Kwon, J.C. Chae, K.Y. Choi, M. Yoo, G.J. Zylstra, Y.M. Kim, B.S. Kang, and E. Kim Appl. Microbiol. Biotechnol. 79 2008 417 422