Model Systems for Flavoenzyme Activity. Regulation of Flavin Recognition via Modulation of Receptor Hydrogen-Bond Donor-Acceptor Properties

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 836-839

  Deans, Robert ^a   Cooke, Graeme ^b   Rotello, Vincent M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001450616     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961877c     Document Type: Article

References (29)

1. Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; Freeman: New York, 1985.
2. Breinlinger, E.; Niemz, A.; Rotello, V. M. J. Am. Chem. Soc. 1995, 117, 5379-5380.
3. For a recent monograph on hydrogen bonding in biological systems see: Jeffrey, G.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer Verlag: Berlin, 1991. For recent model studies of hydrogen bonding in biomimetic systems see: Gallo, E.; Gellman, S. J. Am. Chem. Soc. 1993, 115, 9774-9788. Zimmerman, S.; Murray, T. Tetrahedron Lett. 1994, 4077-4080.
4. For a recent monograph on hydrogen bonding in biological systems see: Jeffrey, G.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer Verlag: Berlin, 1991. For recent model studies of hydrogen bonding in biomimetic systems see: Gallo, E.; Gellman, S. J. Am. Chem. Soc. 1993, 115, 9774-9788. Zimmerman, S.; Murray, T. Tetrahedron Lett. 1994, 4077-4080.
5. For a recent monograph on hydrogen bonding in biological systems see: Jeffrey, G.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer Verlag: Berlin, 1991. For recent model studies of hydrogen bonding in biomimetic systems see: Gallo, E.; Gellman, S. J. Am. Chem. Soc. 1993, 115, 9774-9788. Zimmerman, S.; Murray, T. Tetrahedron Lett. 1994, 4077-4080.
6. Nowick, J.; Chen, J.; Noronha, G. J. Am. Chem. Soc. 1993, 115, 7636-7644.
7. Niemz, A; Rotello, V. M. J. Mol. Rec. 1996, 9, 158-162.
8. For binding of flavins with diaminopyridines see: Shinkai, S.; He, G. X.; Matsuda, T.; Hamilton, A.; Rosenzweig, H. Tetrahedron Lett. 1989, 5895-5898. Tamura, N.; Mitsui, K.; Nabeshima, T.; Yano, Y. J. Chem. Soc., Perkin Trans. 2 1994, 2229-2237. For binding of diaminopyridines to other imides see: Park, T.; Schroeder, J.; Rebek, J. J. Am. Chem. Soc. 1991, 113, 5125-5127. Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561-6562.
9. For binding of flavins with diaminopyridines see: Shinkai, S.; He, G. X.; Matsuda, T.; Hamilton, A.; Rosenzweig, H. Tetrahedron Lett. 1989, 5895-5898. Tamura, N.; Mitsui, K.; Nabeshima, T.; Yano, Y. J. Chem. Soc., Perkin Trans. 2 1994, 2229-2237. For binding of diaminopyridines to other imides see: Park, T.; Schroeder, J.; Rebek, J. J. Am. Chem. Soc. 1991, 113, 5125-5127. Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561-6562.
10. For binding of flavins with diaminopyridines see: Shinkai, S.; He, G. X.; Matsuda, T.; Hamilton, A.; Rosenzweig, H. Tetrahedron Lett. 1989, 5895-5898. Tamura, N.; Mitsui, K.; Nabeshima, T.; Yano, Y. J. Chem. Soc., Perkin Trans. 2 1994, 2229-2237. For binding of diaminopyridines to other imides see: Park, T.; Schroeder, J.; Rebek, J. J. Am. Chem. Soc. 1991, 113, 5125-5127. Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561-6562.
11. For binding of flavins with diaminopyridines see: Shinkai, S.; He, G. X.; Matsuda, T.; Hamilton, A.; Rosenzweig, H. Tetrahedron Lett. 1989, 5895-5898. Tamura, N.; Mitsui, K.; Nabeshima, T.; Yano, Y. J. Chem. Soc., Perkin Trans. 2 1994, 2229-2237. For binding of diaminopyridines to other imides see: Park, T.; Schroeder, J.; Rebek, J. J. Am. Chem. Soc. 1991, 113, 5125-5127. Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561-6562.
12. For a melamine-based flavin receptor see: Tamura, N.; Kajiki, T.; Nabeshima, T.; Yano, Y. J. Chem. Soc., Chem. Commun. 1994, 2583.
13. For other examples of receptors based on diaminopyridine-imide interactions see: Hamilton, A. D.; Van Engen, D. J. Am. Chem. Soc. 1987, 109, 5035. Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561.
14. For other examples of receptors based on diaminopyridine-imide interactions see: Hamilton, A. D.; Van Engen, D. J. Am. Chem. Soc. 1987, 109, 5035. Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561.
15. The MacroModel 4.0 implementation of the AMBER forcefield (AMBER*)was used: Mohamadi, F.; Richards, N.; Guioda, W.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. J. Comput. Chem. 1990, 11, 440.
16. Simons, J.; Saxton, M. Organic Syntheses; Wiley: New York,. 1963; Collect. Vol. IV, p 78.
17. d, the dimerization constant.
18. Chapman, N.; Shorter, J. Correlation Analysis in Chemistry; Plenum: New York, 1978.
19. HG, the chemical shift of the host-guest complex.
20. Beijer, F. H.; Sijbesma, R. P.; Vekemans, J. A. J. M.; Meijer, E. W.; Kooijiman, H.; Spek, A. L. J. Org. Chem. 1996, 61, 6371-6380. Also useful are: Park, T. K.; Feng, Q.; Rebek, J. J. Am. Chem. Soc. 1992, 114, 4529-4532. Willner, I; Rosengaus, J; Biali, S. Tetrahedron Lett. 1992, 3805-3808. Simanek, E. E.; Wazeer, M. I. M.; Mathias, J. P.; Whitesides, G. M. J. Org. Chem. 1994, 59, 4904-4909.
21. Beijer, F. H.; Sijbesma, R. P.; Vekemans, J. A. J. M.; Meijer, E. W.; Kooijiman, H.; Spek, A. L. J. Org. Chem. 1996, 61, 6371-6380. Also useful are: Park, T. K.; Feng, Q.; Rebek, J. J. Am. Chem. Soc. 1992, 114, 4529-4532. Willner, I; Rosengaus, J; Biali, S. Tetrahedron Lett. 1992, 3805-3808. Simanek, E. E.; Wazeer, M. I. M.; Mathias, J. P.; Whitesides, G. M. J. Org. Chem. 1994, 59, 4904-4909.
22. Beijer, F. H.; Sijbesma, R. P.; Vekemans, J. A. J. M.; Meijer, E. W.; Kooijiman, H.; Spek, A. L. J. Org. Chem. 1996, 61, 6371-6380. Also useful are: Park, T. K.; Feng, Q.; Rebek, J. J. Am. Chem. Soc. 1992, 114, 4529-4532. Willner, I; Rosengaus, J; Biali, S. Tetrahedron Lett. 1992, 3805-3808. Simanek, E. E.; Wazeer, M. I. M.; Mathias, J. P.; Whitesides, G. M. J. Org. Chem. 1994, 59, 4904-4909.
23. Beijer, F. H.; Sijbesma, R. P.; Vekemans, J. A. J. M.; Meijer, E. W.; Kooijiman, H.; Spek, A. L. J. Org. Chem. 1996, 61, 6371-6380. Also useful are: Park, T. K.; Feng, Q.; Rebek, J. J. Am. Chem. Soc. 1992, 114, 4529-4532. Willner, I; Rosengaus, J; Biali, S. Tetrahedron Lett. 1992, 3805-3808. Simanek, E. E.; Wazeer, M. I. M.; Mathias, J. P.; Whitesides, G. M. J. Org. Chem. 1994, 59, 4904-4909.
24. The large difference in binding constants between the p-methoxy receptor 1f and the m-methoxy receptor 1g indicate a substantial resonance contribution to the modulation of flavin recognition in these receptors. Due to the complex additivity of the various effects, further analysis was not performed.
25. For a study on the effects of electron-donating and -accepting groups in urea and thiourea binding of sulfonic acids see: Wilcox, C.; Kim, E.; Romano, D.; Kuo, L.; Burt, A.; Curran, D. Tetrahedron 1995, 621-634.
26. Tsai, R. S.; Fan, W.; Tayar, N.; Carrupt, P. A.; Testa, B.; Kier, L. J. Am. Chem. Soc. 1993, 115, 9632-9639. Chen, C. T.; Siegel, J. J. Am. Chem. Soc. 1994, 116, 5959-5960.
27. Tsai, R. S.; Fan, W.; Tayar, N.; Carrupt, P. A.; Testa, B.; Kier, L. J. Am. Chem. Soc. 1993, 115, 9632-9639. Chen, C. T.; Siegel, J. J. Am. Chem. Soc. 1994, 116, 5959-5960.
28. Neder, K.; Whitlock, H. J. Am. Chem. Soc. 1990, 112, 9412-9413.
29. The elemental analysis results for receptor le always showed low nitrogen content. This was attributed to the fact that one of the nitrogen atoms had directly attached oxygens.