Model Systems for Flavoenzyme Activity: Relationships between Cofactor Structure, Binding and Redox Properties

Journal of the American Chemical Society

Volumn 125, Issue 51, 2003, Pages 15789-15795

  Legrand, Yves Marie ^a,b   Gray, Mark ^a   Cooke, Graeme ^b   Rotello, Vincent M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMISTRY; ELECTRONIC EQUIPMENT; FREE ENERGY; SOLVENTS;

BINDING AFFINITY;

ENZYMES;

AMINOPYRIDINE DERIVATIVE; FLAVINE MONONUCLEOTIDE; FLAVOPROTEIN; RECEPTOR; SOLVENT;

ARTICLE; BINDING AFFINITY; ELECTROCHEMICAL ANALYSIS; ENERGY; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME BINDING; ENZYME STRUCTURE; MOLECULAR INTERACTION; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; SYNTHESIS;

ELECTROCHEMISTRY; FLAVINS; KINETICS; OXIDATION-REDUCTION; PYRIDINES; THERMODYNAMICS;

EID: 0346364993     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036940b     Document Type: Article

References (33)

1. Walsh, C. Acc. Chem. Res. 1980, 13, 148-155.
2. Ghisla, S.; Massey, V. Eur. J. Biochem. 1989, 181, 1-17.
3. Bruice, T. C. Isr. J. Chem. 1984, 24, 54-61.
4. Mueller, F. In Topics in Current Chemistry; Boschke, F. L., Ed.; Springer-Verlag: Berlin, 1983; Vol. 108, pp 71-108.
5. Ghisla, S.; Massey, V. Biochem. J. 1986, 239, 1-12.
6. (a) Ghisla, S.; Massey, V.; Lhoste, J. M.; Mayhew, S. G. Biochemistry 1974, 13, 589-597.
7. (b) Muller, F.; Mayhew, S. G.; Massey, V. Biochemistry 1973, 12, 4654-4662.
8. (c) Massey, V.; Ganther, H. Biochemistry 1965, 4, 1161-1173.
9. (d) Ghisla, S.; Massey, V. J. Biol. Chem. 1975, 250, 577-584.
10. (e) Biemann, M.; Claiborne, A.; Ghisla, V.; Massey, V.; Hemmerich, P. J. Biol. Chem. 1983, 258, 5440-5448.
11. See for example: (a) Moore, E. G.; Ghisla, S.; Massey, V. J. Biol. Chem. 1979, 254, 8173-8178.
12. (b) Massey, V.; Ghisla, S.; Moore, E. G. J. Biol. Chem. 1979, 254, 9640-9650.
13. Ludwig, M. L.; Schopfer, L. M.; Metzger, A. L.; Pattridge, K. A.; Massey, V. Biochemistry 1990, 29, 10364-10375.
14. Blankenhom, G. Eur. J. Biochem. 1976, 67, 67-80.
15. Massey, V.; Nishino, T. In Flavins and Flavoproteins; Yagi, K., Yamano, T., Eds.; University Park Press: Baltimore, 1980.
16. Murthy, Y. V. S. N.; Meah, Y.; Massey, V. J. Am. Chem. Soc. 1999, 121, 5344-5345.
17. Hasford, J. J.; Rizzo, C. J. J. Am. Chem. Soc. 1998, 120, 2251-2255.
18. Edmondson, D. E.; Ghisla, S. In Flavins and Flavoproteins 1999; Proceedings of the 13th International Symposium, Konstanz, Germany, August 29-September 4, 1999; Ghisla, S., Kroneck, P., Macheroux, P., Sund, H., Eds.; Rudolf Weber: Agency for Scientific Publications, 1999; pp 71-76.
19. For flavin electrochemical processes under aqueous conditions see: (a) Muller, F. In Chemistry and Biochemistry of Flavoenzymes; Muller, F., Ed.; CRC Press: Boca Raton, FL, 1991; Vol. 1, pp 1-71.
20. (b) Stankovich, M. T. In Chemistry and Biochemistry of Flavoenzymes; Muller, F., Ed.; CRC Press: Boca Raton, FL. 1991: Vol. 1, pp 401-425.
21. Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 44-52.
22. For studies featuring multipoint interactions between flavin analogues and artificial receptors, see: Kajiki, T.; Moriya, H.; Hoshino, K.; Kuroi, T.; Kondo, S.; Nabeshima, T.; Yano, Y. J. Org. Chem. 1999, 64, 9679-9689.
23. 2) due to their suitability for NMR and electrochemical work, respectively. Previously, we have shown that neither the interchange between these solvents nor the presence of the electrolyte necessary for conducting the electrochemical experiments has any measurable effect on the results obtained. See: Deans, R.; Niemz, A.; Breinlinger, E. C.; Rotello, V. M. J. Am. Chem. Soc. 1997, 119, 10863-10864.
24. (a) Stone, A. J. The Theory of Intermolecular Forces; Clarendon Press: Oxford, 1996.
25. (b) Scheiner, S. Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: New York, 1997.
26. Breinlinger, E.; Niemz, A.; Rotello, V. M. J. Am. Chem. Soc. 1995, 117, 5379-5380.
27. For substituent effects and hydrogen bonding, see: Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621-634.
28. Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207.
29. Niemz, A.; Imbriglio, J.; Rotello, V. M. J. Am. Chem. Soc. 1997, 119, 887-892.
30. Niemz, A.; Rotello, V. M. J. Am. Chem. Soc. 1997, 119, 6833-6836.
31. NMR dilution experiments show that DAP and the flavins do not dimerize or aggregate under the experimental conditions used in our study.
32. Long, J. R.; Drago, R. S. J. Chem. Soc. 1982, 59, 1037-1039.
33. For further information see: Conners, K. Binding Constants; Wiley and Sons: New York, 1987.