Theoretical exploration of the mechanism of riboflavin formation from 6,7-dimethyl-8-ribityllumazine: Nucleophilic catalysis, hydride transfer, hydrogen atom transfer, or nucleophilic addition?

Journal of the American Chemical Society

Volumn 135, Issue 17, 2013, Pages 6658-6668

  Breugst, Martin ^a   Eschenmoser, Albert ^b   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL RESULTS; ENERGY TRANSITION STATE; HYDRIDE TRANSFERS; HYDROGEN-ATOM TRANSFER; MECHANISTIC PATHWAYS; MOLECULAR TRANSFORMATION; NUCLEOPHILIC ADDITIONS; NUCLEOPHILIC CATALYSIS;

ADDITION REACTIONS; ATOMS; DENSITY FUNCTIONAL THEORY; HYDRIDES; HYDROGEN; MOLECULES; SYNTHESIS (CHEMICAL);

CATALYSIS;

HYDROGEN; RIBOFLAVIN;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CYCLIZATION; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIMERIZATION; ELECTROPHILICITY; ENTROPY; ENZYME ACTIVE SITE; HYDROGEN BOND; ISOMERIZATION; NONHUMAN; NUCLEOPHILICITY; PH; PROTON TRANSPORT; SOLVATION; STEREOCHEMISTRY; TAUTOMERIZATION;

CATALYSIS; CYCLIZATION; ENERGY TRANSFER; HYDROGEN; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MONTE CARLO METHOD; PROTONS; PTERIDINES; RIBOFLAVIN; SOLVENTS; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; WATER;

EID: 84877029447     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja402099f     Document Type: Article

References (48)

1. Plaut, G. W. E. J. Biol. Chem. 1960, 235, PC41-PC42
2. Plaut, G. W. E. J. Biol. Chem. 1963, 238, 2225-2243
3. Wacker, H.; Harvey, R. A.; Winestock, C. H.; Plaut, G. W. E. J. Biol. Chem. 1964, 239, 3493-3497
4. Plaut, G. W. E.; Beach, R. L.; Aogaichi, T. Biochemistry 1970, 9, 771-785
5. Rowan, T.; Wood, H. C. S. Proc. Chem. Soc. 1963, 21-22
6. Beach, R.; Plaut, G. W. E. Tetrahedron Lett. 1969, 10, 3489-3492
7. Paterson, T.; Wood, H. C. S. J. Chem. Soc. D 1969, 290-291
8. Paterson, T.; Wood, H. C. S. J. Chem. Soc., Perkin Trans. 1 1972, 1051-1056
9. Truffault, V.; Coles, M.; Diercks, T.; Abelmann, K.; Eberhardt, S.; Lüttgen, H.; Bacher, A.; Kessler, H. J. Mol. Biol. 2001, 309, 949-960
10. Neuberger, G.; Bacher, A. Biochem. Biophys. Res. Commun. 1985, 127, 175-181
11. Talukdar, A.; Zhao, Y.; Lv, W.; Bacher, A.; Illarionov, B.; Fischer, M.; Cushman, M. J. Org. Chem. 2012, 77, 6239-6261
12. Rowan, T.; Wood, H. C. S. J. Chem. Soc. C 1968, 452-458
13. Gerhardt, S.; Schott, A.-K.; Kairies, N.; Cushman, M.; Illarionov, B.; Eisenreich, W.; Bacher, A.; Huber, R.; Steinbacher, S.; Fischer, M. Structure 2002, 10, 1371-1381
14. Illarionov, B.; Eisenreich, W.; Bacher, A. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 7224-7229
15. Illarionov, B.; Haase, I.; Bacher, A.; Fischer, M.; Schramek, N. J. Biol. Chem. 2003, 278, 47700-47706
16. Kim, R.-R.; Illarionov, B.; Joshi, M.; Cushman, M.; Lee, C. Y.; Eisenreich, W.; Fischer, M.; Bacher, A. J. Am. Chem. Soc. 2010, 132, 2983-2990
17. MacroModel, version 9.9; Schrödinger, LLC: New York, 2012.
18. Zhao, Y.; Truhlar, D. Theor. Chem. Acc. 2008, 120, 215-241
19. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
20. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
21. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
22. Cancès, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032-3041
23. Ribeiro, R. F.; Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2011, 115, 14556-14562
24. Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799-805
25. Andzelm, J.; Kölmel, C.; Klamt, A. J. Chem. Phys. 1995, 103, 9312-9320
26. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001
27. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681
28. Takano, Y.; Houk, K. N. J. Chem. Theory Comput. 2005, 1, 70-77
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision C.01; Gaussian, Inc.: Wallingford, CT, 2009.
30. Ramsperger, A.; Augustin, M.; Schott, A.-K.; Gerhardt, S.; Krojer, T.; Eisenreich, W.; Illarionov, B.; Cushman, M.; Bacher, A.; Huber, R.; Fischer, M. J. Biol. Chem. 2006, 281, 1224-1232
31. McAndless, J. M.; Stewart, R. Can. J. Chem. 1970, 48, 263-270
32. Mammen, M.; Shakhnovich, E. I.; Deutch, J. M.; Whitesides, G. M. J. Org. Chem. 1998, 63, 3821-3830
33. Strajbl, M.; Sham, Y. Y.; Villà, J.; Chu, Z.-T.; Warshel, A. J. Phys. Chem. B 2000, 104, 4578-4584
34. Zhou, H.-X.; Gilson, M. K. Chem. Rev. 2009, 109, 4092-4107
35. Nagel, Z. D.; Klinman, J. P. Chem. Rev. 2006, 106, 3095-3118
36. Hammes, G. G.; Benkovic, S. J.; Hammes-Schiffer, S. Biochemistry 2011, 50, 10422-10430
37. McGeagh, J. D.; Ranaghan, K. E.; Mulholland, A. J. Biochim. Biophys. Acta 2011, 1814, 1077-1092
38. Haines, B. E.; Steussy, C. N.; Stauffacher, C. V.; Wiest, O. Biochemistry 2012, 51, 7983-7995
39. Wu, Y. D.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 906-908
40. Wu, Y. D.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 2353-2358
41. Wu, Y.-D.; Lai, D. K. W.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 4100-4108
42. Zheng, Y.-J.; Jordan, D. B.; Liao, D.-I. Bioorg. Chem. 2003, 31, 278-287
43. Kim, H. J.; Ruszczycky, M. W.; Choi, S.-h.; Liu, Y.-n.; Liu, H.-w. Nature 2011, 473, 109-112
44. Kelly, W. L. Nature 2011, 473, 35-36
45. Kim, H. J.; Ruszczycky, M. W.; Liu, H.-w. Curr. Opin. Chem. Biol. 2012, 16, 124-131
46. Hess, B. A., Jr.; Smentek, L. Org. Biomol. Chem. 2012, 10, 7503-7509
47. Camaioni, D. M.; Autrey, S. T.; Salinas, T. B.; Franz, J. A. J. Am. Chem. Soc. 1996, 118, 2013-2022
48. Dybala-Defratyka, A.; Paneth, P.; Pu, J.; Truhlar, D. G. J. Phys. Chem. A 2004, 108, 2475-2486