Model systems for flavoenzyme activity: Site-isolated redox behavior in flavin-functionalized random polystyrene copolymers

Organic Letters

Volumn 7, Issue 13, 2005, Pages 2551-2554

  Carroll, Joseph B ^a   Jordan, Brian J ^a   Xu, Hao ^a   Erdogan, Belma ^a   Lee, Lisa ^a   Cheng, Lily ^a   Tiernan, Christopher ^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

POLYSTYRENE DERIVATIVE; PYRIDINE DERIVATIVE; RIBOFLAVIN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; KINETICS; METABOLISM; METHODOLOGY; OXIDATION REDUCTION REACTION; THERMODYNAMICS;

ELECTROCHEMISTRY; FLAVINS; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POLYSTYRENES; PYRIDINES; THERMODYNAMICS;

EID: 29844457002     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0505407     Document Type: Article

References (32)

1. (a) Chaiyen, P.; Sucharitakul, J.; Svasti, J.; Entsch, B.; Massey, V.; Ballou, D. P. Biochemistry 2004, 43, 3933-3943.
2. (b) Chakraborty, S.; Massey, V. J. Biol. Chem. 2002, 277, 41507-41516.
3. (a) Reddy, S. Y.; Bruice, T. C. Protein Sci. 2004, 13, 1965-1978.
4. (b) Anthony, C. Biochem. J. 1996, 320, 697-711.
5. Sundaresan, V.; Chartron, J.; Yamaguchi, M.; Stout, C. D. J. Mol. Biol. 2005, 346, 617-629.
6. Pey, A. L.; Thorolfsson, M.; Teigen, K.; Ugarte, M.; Martinez, A. J. Am. Chem. Soc. 2004, 126, 13670-13678.
7. (a) Liu, Y.; Flood, A. H.; Stoddart, J. F. J. Am. Chem. Soc. 2004, 126, 9150-9151.
8. (b) Lehn, J. M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, 1995.
9. (c) Kaifer, A. E.; Gomez-Kaifer, M. Supramolecular Electrochemistry, Wiley-VCH: Weinheim, 1999.
10. (a) Hasford, J. J.; Rizzo, C. J. J. Am. Chem. Soc. 1998, 120, 2251-2255.
11. (b) Kajiki, T.; Moriya, H.; Hoshino, K.; Kuroi, T.; Kondo, S.; Nabeshima, T.; Yano, Y. J. Org. Chem. 1999, 64, 9679-9689.
12. (c) Deans, R.; Rotello, V. M. J. Org. Chem. 1997, 62, 4528-4529.
13. (d) Greaves, M. D.; Rotello, V. M. J. Am. Chem. Soc. 1997, 119, 10569-10572.
14. (e) Legrand, Y. M.; Gray, M.; Cooke, G.; Rotello, V. M. J. Am. Chem. Soc. 2003, 125, 15789-15795.
15. (f) Gray, M.; Goodman, A. J.; Carroll, J. B.; Bardon, K.; Markey, M.; Cooke, G.; Rotello, V. M. Org. Lett. 2004, 6, 385-388.
16. (a) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097.
17. (b) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426.
18. (c) McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537-2574.
19. (d) Pollino, J. M.; Stubbs, L. P.; Weck, M. J. Am. Chem. Soc. 2004, 126, 563-567.
20. (e) Ilhan, F.; Gray, M.; Rotello, V. M. Macromolecules 2001, 34, 2597-2601.
21. (a) Huisgen, R. Pure Appl. Chem. 1989, 61, 613-628.
22. (b) Huisgen, R.; Szeimies, G.; Mobius, L. Chem. Ber. 1967, 100, 2494-2507.
23. (c) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
24. (d) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
25. Extreme caution was exercised in preparation of electrolyte solutions for CV studies: Sax, N. I.; Lewis, R. J. Dangerous Properties of Industrial Materials, 7th ed.; Van Nostrand Reinhold: New York, 1989; Vol. 3.
26. -1.
27. Niemz, A.; Imbriglio, J.; Rotello, V. M. J. Am. Chem. Soc. 1997, 119, 887-892.
28. (a) Galow, T. H.; Ilhan, F.; Cooke, G.; Rotello, V. M. J. Am. Chem. Soc. 2000, 122, 3595-3598.
29. (b) Gorman, C. B. Adv. Mater. 1998, 10, 295-308.
30. (c) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71.
31. (d) Dandliker, P. J.; Diederich, F.; Gross, M.; Knobler, C. B.; Louati, A.; Sanford, E. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1739-1741.
32. (e) Dandliker, P. J.; Diederich, F.; Gisselbrecht, J.-P.; Louati, A.; Gross, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2725-2728.