Polymeric enzyme mimics: Catalytic activity of ribose-containing polymers for a phosphate substrate

Organic and Biomolecular Chemistry

Volumn 1, Issue 13, 2003, Pages 2276-2282

  Han, Man Jung ^a   Yoo, Kyung Soo ^a   Kim, Young Heui ^a   Chang, Ji Young ^b  

^a Ajou University   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; ENZYMES; ESTERS; HYDROGEN BONDS; HYDROLYSIS; REACTION KINETICS; SUBSTRATES;

REVERSE REACTIONS;

BIOCHEMISTRY;

ACETIC ACID; ENZYME INHIBITOR; ETHYL 4-NITROPHENYL METHYLPHOSPHONATE; METHYLPHOSPHONIC ACID ETHYL 4 NITROPHENYL ESTER; ORGANOPHOSPHATE; ORGANOPHOSPHORUS COMPOUND; PHOSPHATE; POLYMER; POTASSIUM DERIVATIVE; POTASSIUM DIHYDROGEN PHOSPHATE; RIBOSE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ENZYME SPECIFICITY; HYDROLYSIS; KINETICS; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORYLATION; SYNTHESIS; TIME;

CATALYSIS; ENZYME INHIBITORS; HYDROLYSIS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHATES; PHOSPHORIC ACID ESTERS; PHOSPHORYLATION; POLYMERS; POTASSIUM COMPOUNDS; RIBOSE; SODIUM ACETATE; SUBSTRATE SPECIFICITY; TIME FACTORS;

EID: 0042307432     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b301166f     Document Type: Article

References (33)

1. T. Kunitake and Y. Okahata, Adv. Polym. Sci., 1976, 20, 159-221.
2. T. Kunitake, in Polymer-supported Reactions in Organic Synthesis, ed. P. Hodge and D. C. Sherrington, John Wiley & Sons, New York, 1980, pp. 195-245.
3. C. G. Overberger, T. St. Pierre, N. Vorchheimer and S. Yaroslavsky, J. Am. Chem. Soc., 1963, 85, 3513-3515.
4. C. G. Overberger and T. W. Smith, Macromolecules, 1975, 8, 416-424.
5. I. Klotz, in Enzyme Models-Synthetic Polymers, ed. A. Williams and M. Page, The Royal Society of Chemistry, London, 1987, pp. 14-34.
6. J. Suh, I. S. Scarpa and I. M. Klotz, J. Am. Chem. Soc., 1976, 98, 7060-7064.
7. F. Hollfelder, A. Kirby and D. Tawfik, J. Org. Chem., 2001, 66, 5866-5874.
8. F. Hollfelder, A. Kirby and D. Tawfik, J. Am. Chem. Soc., 1997, 119, 9578-9579.
9. L. Liu, M. Rozenman and R. Breslow, J. Am. Chem. Soc., 2002, 124, 12660-12661.
10. C. Guerrier-Takada and S. Altman, Science, 1983, 223, 285-286.
11. R. R. Breaker and G. F. Joyce, Chem. Biol., 1994, 1, 223-229.
12. M. J. Han, K. S. Yoo, J. Y. Chang and T.-K. Ha, Angew. Chem., 2000, 112, 355-357 (Angew. Chem., Int. Ed., 2000, 39, 347-349).
13. T.-K. Ha, O. M. Suleimenov and M. J. Han, J. Mol. Struct. (THEOCHEM), 2001, 574, 75-83.
14. M. J. Han, K. S. Yoo, Y. H. Kim and J. Y Chang, Tetrahedron Lett., 2002, 43, 5597-5600.
15. H. Sasaio, K. Matsuno and T. Suami, J. Carbohydr. Chem., 1985, 4, 99-112.
16. F. Weygand and F. Wirth, Chem. Ber., 1952, 85, 1000-1007.
17. (a) R. Breslow and D.-H. Huang, Proc. Natl. Acad. Sci. U. S. A., 1991, 88, 4080-4083.
18. (b) A. Sreedhara, A. Patwardhan and J. A. Cowan, Chem. Commun., 1999, 1147-1148.
19. (c) J. Rammo and H.-J. Schneider, Liebigs Ann. Chem., 1996, 1757-1767.
20. (a) M. J. Han, K. S. Yoo, T. J. Cho, J. Y. Chang, Y. J. Cha and S. H. Nam, Chem. Commun., 1997, 163-164.
21. (b) M. J. Han, K. S. Yoo, K. H. Kim, G. H. Lee and J. Y. Chang, Macromolecules, 1997, 30, 5408-5415.
22. The mole concentration of ribose is same as the ribose residue concentration of the polymer.
23. R. Breslow, J. B. Doherty, G. Guillot and C. Lipsey, J. Am. Chem. Soc., 1978, 100, 3227-3229.
24. R. Breslow, P. Bovy and C. L. Hersh, J. Am. Chem. Soc., 1980, 102, 2115-2117.
25. P. Chambon, J. D. Weill, J. Doly, M. T. Strosser and P. Mandel, Biochem. Biophys. Res. Commun., 1966, 215, 638-643.
26. T. Sugimura, S. Fujimura, S. Hasegawa and Y. Kawamura, Biochim. Biophys. Acta, 1967, 138, 438-441.
27. K. Ueda and O. Hayaishi, Ann. Rev. Biochem., 1985, 54, 73-100.
28. D. Lautier, J. Lagueux, J. Thibodeau, L. Menard and G. G. Poirier, Mol. Cell. Biochem., 1993, 122, 171-193.
29. R. Alvarez-Gonzalez, G. Pacheco-Rodriguez and H. Mendoza-Alvarez, Mol. Cell. Biochem., 1994, 138, 33-37.
30. H. Maruta, N. Matsumura and S. Tanuma, Biochem. Biophys. Res. Commun., 1997, 236, 265-269.
31. C. M. Simbulan-Rosenthal, D. S. Rosenthal, S. Iyer, A. H. Boulares and M. E. Smulson, J. Biol. Chem., 1998, 273, 13703-13712.
32. M. Malanga and F. R. Althaus, J. Biol. Chem., 1994, 269, 17691-17696.
33. M. S. Satoh, G. G. Poirier and T. Lindahl, Biochemistry, 1994, 33, 7099-7106.