Quantum mechanical/molecular mechanical study on the mechanism of the enzymatic Baeyer-Villiger reaction

Journal of the American Chemical Society

Volumn 134, Issue 5, 2012, Pages 2732-2741

  Polyak, Iakov ^a   Reetz, Manfred T ^a,b   Thiel, Walter ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANIONIC CHARACTER; BAEYER-VILLIGER REACTION; CATALYTIC EFFICIENCIES; COFACTORS; CONFORMATIONAL PREFERENCES; CYCLOHEXANONE MONOOXYGENASE; CYCLOHEXANONES; ENERGY PROFILE; FORCE FIELDS; FREE-ENERGY CALCULATIONS; GASPHASE; GEOMETRY OPTIMIZATION; MOLECULAR DYNAMICS SIMULATIONS; QM/MM CALCULATIONS; QUANTUM MECHANICAL/MOLECULAR MECHANICAL STUDIES; REACTION PATH CALCULATION; SEMI-EMPIRICAL; SIDE-CHAINS; TRANSITION STATE;

ADDITION REACTIONS; AMIDES; CATALYSIS; CATALYTIC OXIDATION; ENERGY BARRIERS; ENZYMES; HYDROGEN BONDS; MOLECULAR DYNAMICS; MOLECULAR MODELING; QUANTUM CHEMISTRY;

REACTION INTERMEDIATES;

CYCLOHEXANONE DERIVATIVE; CYCLOHEXANONE MONOOXYGENASE; NICOTINAMIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ADDITION REACTION; ARTICLE; BAEYER VILLIGER REACTION; BINDING SITE; CATALYSIS; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; ENERGY; ENZYME ACTIVE SITE; ENZYME METABOLISM; GAS; HYDROGEN BOND; MOLECULAR MECHANICS; NONHUMAN; PHASE TRANSITION; QUANTUM MECHANICS; RHODOCOCCUS;

BIOCATALYSIS; CYCLOHEXANONES; LACTONES; OXYGENASES; QUANTUM THEORY;

EID: 84856732583     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2103839     Document Type: Article

References (96)

1. Baeyer, A.; Villiger, V. Ber. Dtsch. Chem. Ges. 1899, 32, 3625-3633
2. Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848-1849
3. Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442-3451
4. Strukul, G. Angew. Chem., Int. Ed. 1998, 37, 1199-1209
5. Uchida, T.; Katsuki, T. Tetrahedron Lett. 2001, 42, 6911-6914
6. Ito, K.; Ishii, A.; Kuroda, T.; Katsuki, T. Synlett 2003, 643-646
7. Frison, J.-C.; Palazzi, C.; Bolm, C. Tetrahedron 2006, 62, 6700-6706
8. Colladon, M.; Scarso, A.; Strukul, G. Synlett 2006, 3515-3520
9. Murahashi, S.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368
10. Imada, Y.; Iida, H.; Murahashi, S.; Naota, T. Angew. Chem., Int. Ed. 2005, 44, 1704-1706
11. Wang, B.; Shen, Y.-M.; Shi, Y. J. Org. Chem. 2006, 71, 9519-9521
12. Peris, G.; Miller, S. J. Org. Lett. 2008, 10, 3049-3052
13. Malkov, A. V.; Friscourt, F.; Bell, M.; Swarbrick, M. E.; Kocovsky, P. J. Org. Chem. 2008, 73, 3996-4003
14. Xu, S.; Wang, Z.; Zhang, X.; Zhang, X.; Ding, K. Angew. Chem., Int. Ed. 2008, 47, 2840-2843
15. Mihovilovic, M.; Muller, B.; Stanetty, P. Eur. J. Org. Chem. 2002, 3711-3730
16. Wohlgemuth, R. Eng. Life Sci. 2006, 6, 577-583
17. Rehdorf, J.; Bornscheuer, M. Monooxygenases, Baeyer Villiger Applications in Organic Synthesis; John Wiley & Sons: Hoboken, NJ, 2009.
18. de Gonzalo, G.; Mihovilovic, M. D.; Fraaije, M. W. ChemBioChem 2010, 11, 2208-2231
19. Pazmino, D. E. T.; Dudek, H. M.; Fraaije, M. W. Curr. Opin. Chem. Biol. 2010, 14, 138-144
20. Leisch, H.; Morley, K.; Lau, P. Chem. Rev. 2011, 111, 4165-4222
21. Kayser, M. M. Tetrahedron 2009, 65, 947-974
22. Review of directed evolution of enantioselective enzymes as catalysts in organic chemistry: Reetz, M. T. Angew. Chem., Int. Ed. 2011, 50, 138-174
23. Kayser, M. M.; Clouthier, C. M. J. Org. Chem. 2006, 71, 8424-8430
24. Reetz, M.; Brunner, B.; Schneider, T.; Schulz, F.; Clouthier, C.; Kayser, M. Angew. Chem., Int. Ed. 2004, 43, 4075-4078
25. Bocola, M.; Schulz, F.; Leca, F.; Vogel, A.; Fraaije, M.; Reetz, M. Adv. Synth. Catal. 2005, 347, 979-986
26. Mihovilovic, M.; Rudroff, F.; Winninger, A.; Schneider, T.; Schulz, F.; Reetz, M. Org. Lett. 2006, 8, 1221-1224
27. Clouthier, C. M.; Kayser, M. M.; Reetz, M. T. J. Org. Chem. 2006, 71, 8431-8437
28. Reetz, M. T.; Wu, S. J. Am. Chem. Soc. 2009, 131, 15424-15432
29. Wu, S.; Acevedo, J. P.; Reetz, M. T. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 2775-2780
30. Kirschner, A.; Bornscheuer, U. T. Angew. Chem., Int. Ed. 2006, 45, 7004-7006
31. Kirschner, A.; Bornscheuer, U. T. Appl. Microbiol. Biotechnol. 2008, 81, 465-472
32. Rehdorf, J.; Mihovilovic, M. D.; Bornscheuer, U. T. Angew. Chem., Int. Ed. 2010, 49, 4506-4508
33. Turfitt, G. Biochem. J. 1948, 42, 376-383
34. Donoghue, N.; Norris, D.; Trudgill, P. Eur. J. Biochem. 1976, 63, 175-192
35. Chen, Y.; Peoples, O.; Walsh, C. J. Bacteriol. 1988, 170, 781-789
36. Ryerson, C.; Ballou, D.; Walsh, C. Biochemistry 1982, 21, 2644-2655
37. Walsh, C.; Chen, Y. Angew. Chem., Int. Ed. Engl. 1988, 27, 333-343
38. Brzostowicz, P.; Walters, D.; Thomas, S.; Nagarajan, V.; Rouviere, P. Appl. Environ. Microbiol. 2003, 69, 334-342
39. Sheng, D.; Ballou, D.; Massey, V. Biochemistry 2001, 40, 11156-11167
40. Pazmino, D. E. T.; Baas, B.-J.; Janssen, D. B.; Fraaije, M. W. Biochemistry 2008, 47, 4082-4093
41. Orru, R.; Dudek, H. M.; Martinoli, C.; Pazmino, D. E. T.; Royant, A.; Weik, M.; Fraaije, M. W.; Mattevi, A. J. Biol. Chem. 2011, 286, 29284-29291
42. Mirza, I. A.; Yachnin, B. J.; Wang, S.; Grosse, S.; Bergeron, H.; Imura, A.; Iwaki, H.; Hasegawa, Y.; Lau, P. C. K.; Berghuis, A. M. J. Am. Chem. Soc. 2009, 131, 8848-8854
43. Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737-750
44. ten Brink, G.; Arends, I.; Sheldon, R. Chem. Rev. 2004, 104, 4105-4123
45. Okuno, Y. Chem.-Eur. J. 1997, 3, 212-218
46. Grein, F.; Chen, A.; Edwards, D.; Crudden, C. J. Org. Chem. 2006, 71, 861-872
47. Alvarez-Idaboy, J.; Reyes, L.; Cruz, J. Org. Lett. 2006, 8, 1763-1765
48. Alvarez-Idaboy, J. R.; Reyes, L.; Mora-Diez, N. Org. Biomol. Chem. 2007, 5, 3682-3689
49. Alvarez-Idaboy, J. R.; Reyes, L. J. Org. Chem. 2007, 72, 6580-6583
50. Mora-Diez, N.; Keller, S.; Alvarez-Idaboy, J. R. Org. Biomol. Chem. 2009, 7, 3682-3690
51. Malito, E.; Alfieri, A.; Fraaije, M.; Mattevi, A. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 13157-13162
52. Gordon, J.; Myers, J.; Folta, T.; Shoja, V.; Heath, L.; Onufriev, A. Nucleic Acids Res. 2005, 33, W368-W371
53. Anandakrishnan, R.; Onufriev, A. J. Comp. Biol. 2008, 15, 165-184
54. Li, H.; Robertson, A.; Jensen, J. Proteins 2005, 61, 704-721
55. MacKerell, A. J. Phys. Chem. B 1998, 102, 3586-3616
56. Brooks, B.; Bruccoleri, R.; Olafson, D.; States, D.; Swaminathan, S.; Karplus, M. J. Comput. Chem. 1983, 4, 187-217
57. Brooks, B. R. J. Comput. Chem. 2009, 30, 1545-1614
58. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. J. Comput. Chem. 1998, 19, 1639-1662
59. Warshel, A.; Levitt, M. J. Mol. Biol. 1976, 103, 227-249
60. Senn, H. M.; Thiel, W. Angew. Chem., Int. Ed. 2009, 48, 1198-1229
61. Slater, J. Phys. Rev. 1953, 91, 528-530
62. Vosko, S.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211
63. Becke, A. Phys. Rev. A 1988, 38, 3098-3100
64. Becke, A. J. Chem. Phys. 1993, 98, 5648-5652
65. Stephens, P.; Devlin, F.; Chabalowski, C.; Frisch, M. J. Phys. Chem. 1994, 98, 11623-11627
66. Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 37, 785-789
67. Bakowies, D.; Thiel, W. J. Phys. Chem. 1996, 100, 10580-10594
68. de Vries, A.; Sherwood, P.; Collins, S.; Rigby, A.; Rigutto, M.; Kramer, G. J. Phys. Chem. B 1999, 103, 6133-6141
69. Sherwood, P.; de Vries, A.; Collins, S.; Greatbanks, S.; Burton, N.; Vincent, M.; Hillier, I. Farad. Disc. 1997, 106, 79-92
70. Sherwood, P. J. Mol. Struct. (Theochem) 2003, 632, 1-28
71. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Chem. Phys. Lett. 1989, 162, 165-169
72. Smith, W.; Forester, T. J. Mol. Graph. 1996, 14, 136-141
73. Billeter, S.; Turner, A.; Thiel, W. Phys. Chem. Chem. Phys. 2000, 2, 2177-2186
74. Kästner, J.; Carr, J. M.; Keal, T. W.; Thiel, W.; Wander, A.; Sherwood, P. J. Phys. Chem. A 2009, 113, 11856-11865
75. Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577
76. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829-5835
77. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
78. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
79. Nocedal, J. Math. Comp. 1980, 35, 773-782
80. Liu, D.; Nocedal, J. Math. Programming 1989, 45, 503-528
81. Banerjee, A.; Adams, N.; Simons, J.; Shepard, R. J. Phys. Chem. 1985, 89, 52-57
82. Baker, J. J. Comput. Chem. 1986, 7, 385-395
83. Nose, S. J. Chem. Phys. 1984, 81, 511-519
84. Hoover, W. Phys. Rev. A 1985, 31, 1695-1697
85. Scholten, M. Ph.D. thesis, Universität Düsseldorf, 2003.
86. Otte, N.; Scholten, M.; Thiel, W. J. Phys. Chem. A 2007, 111, 5751-5755
87. Ryckaert, J.; Ciccotti, G.; Berendsen, H. J. Comput. Phys. 1977, 23, 327-341
88. Senn, H. M.; Thiel, S.; Thiel, W. J. Chem. Theory Comput. 2005, 1, 494-505
89. Lonsdale, R.; Harvey, J. N.; Mulholland, A. J. J. Phys. Chem. Lett. 2010, 1, 3232-3237
90. Krow, G. Tetrahedron 1981, 37, 2697-2724
91. Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309
92. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136
93. Kelly, D. R. Tetrahedron: Asymmetry 1996, 7, 1149-1152
94. Stewart, J. Curr. Org. Chem. 1998, 2, 195-216
95. Stewart, J.; Reed, K.; Martinez, C.; Zhu, J.; Chen, G.; Kayser, M. J. Am. Chem. Soc. 1998, 120, 3541-3548
96. Potts, A.; Baer, T. J. Mol. Struct. (Theochem) 1997, 419, 11-18