Cleavage of an RNA model catalyzed by dinuclear Zn(II) complexes containing rate-accelerating pendants. Comparison of the catalytic benefits of H-bonding and hydrophobic substituents

Journal of Organic Chemistry

Volumn 75, Issue 24, 2010, Pages 8471-8477

  Mohamed, Mark F ^a   Brown, R Stan ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDO; AMINE LIGAND; CATALYTIC RATES; CONTROLLED CONDITIONS; DINUCLEAR; DINUCLEAR COMPLEX; H-BONDING; HYDROPHOBIC SUBSTITUENTS; LOCAL POLARITY; METAL COMPLEXING; METHYL GROUP; P-NITROPHENYL PHOSPHATE; PH OPTIMA; RELATED SYSTEMS; RING SUBSTITUENTS; SATURATION KINETICS; SECOND ORDERS; STERIC EFFECT; SUBSTRATE BINDING; ZN COMPLEX;

CATALYSIS; CATALYSTS; FUNCTIONAL GROUPS; LIGANDS; METHANOL; RNA; ZINC; ZINC COMPOUNDS;

RATE CONSTANTS;

2 HYDROXYPROPYL 4 NITROPHENYL PHOSPHATE; ACETAMIDE DERIVATIVE; AMINE; AMINO ACID DERIVATIVE; HYDROGEN; METAL COMPLEX; METHANOL; NITROBENZENE DERIVATIVE; PYRIDINE; RNA; UNCLASSIFIED DRUG; ZINC COMPLEX;

ARTICLE; BINDING AFFINITY; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; CROSS LINKING; CYCLIZATION; DECOMPOSITION; HYDROGEN BOND; HYDROPHOBICITY; KINETICS; POLARIZATION; RNA CLEAVAGE; SUBSTITUTION REACTION; SYNTHESIS; TRANSESTERIFICATION;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; KINETICS; LIGANDS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; RNA; ZINC;

EID: 78650367835     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1017316     Document Type: Article

References (50)

1. Schroeder, G. K.; Lad, C.; Wyman, P.; Williams, N. H.; Wolfenden, R. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 4052
2. For a representative list of references on various metal-containing complexes, see: Mancin, F.; Tecillia, P. New J. Chem. 2007, 31, 800
3. Weston, J. Chem. Rev. 2005, 105, 2151
4. Molenveld, P.; Engbertsen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75
5. Williams, N. H.; Takasaki, B.; Wall, M.; Chin, J. Acc. Chem. Res. 1999, 32, 485
6. Mancin, F.; Scrimin, P.; Tecilla, P.; Tonellato, U. Chem. Commun. 2005, 2540
7. Morrow, J. R.; Iranzo, O. Curr. Opin. Chem.Biol. 2004, 8, 192
8. Borovik, A. S. Acc. Chem. Res. 2005, 38, 54
9. Marque Rivas, J. C. Curr. Org. Chem. 2007, 11, 1434
10. For a representative example of studies on small molecule enzyme mimics utilizing hydrogen bond donors, see: Feng, G.; Natale, D.; Prabaharan, R.; Marque-Rivas, J. C.; Williams, N. H. Angew. Chem., Int. Ed. 2006, 45, 7056
11. Feng, G.; Marque-Rivas, J. C.; Williams, N. H. Chem. Commun. 2006, 1845
12. Aït-Haddou, H.; Sumaoka, J.; Wiskur, S. L.; Folmer-Anderson, J. F.; Anslyn, E. V. Angew. Chem., Int. Ed. 2002, 41, 4014
13. Livieri, M.; Mancin, F.; Tonellato, U.; Chin, J. Chem. Commun. 2004, 2862
14. Feng, G.; Marque-Rivas, J. C.; Torres Martin de Rosales, R.; Williams, N. H. J. Am. Chem. Soc. 2005, 127, 13470
15. Lombardo, V.; Bonomi, R.; Sissi, C.; Mancin, F. Tetrahedron 2010, 66, 2189
16. Bonomi, R.; Saielli, G.; Tonellato, U.; Scrimin, P.; Mancin, F. J. Am. Chem. Soc. 2009, 131, 11278
17. Bonomi, R.; Selvestrel, F.; Lombardo, V.; Sissi, C.; Polizzi, S.; Mancin, F.; Tonellato, U.; Scrimin, P. J. Am. Chem. Soc. 2008, 130, 15744
18. Livieri, M.; Mancin, F.; Saielli, G.; Chin, J.; Tonellato, U. Chem.-Eur. J. 2007, 13, 2246
19. +-complex catalyzed alcoholysis reactions of phosphoryl transfer reactions. In Progress in Inorganic Chemistry; Karlin, K. D., Ed.; John Wiley and Sons: Hoboken, NJ, Vol. 57, in press.
20. Neverov, A. A.; Lu, Z.-L.; Maxwell, C. I.; Mohamed, M. F.; White, C. J.; Tsang, J. S. W.; Brown, R. S. J. Am. Chem. Soc. 2006, 128, 16398
21. Bunn, S. E.; Liu, C. T.; Lu, Z.-L.; Neverov, A. A.; Brown, R. S. J. Am. Chem. Soc. 2007, 129, 16238
22. Liu, C. T.; Neverov, A. A.; Brown, R. S. J. Am. Chem. Soc. 2008, 130, 16711
23. 2 is no more reactive in water than its mononuclear analogue, the Zn(II) complex of 1,5,9-triazacyclododecane for the cleavage of bis- p -nitrophenyl phosphate.
24. Stockbridge, R. B.; Wolfenden, R. Chem. Commun. 2010, 46, 4306
25. See also: Stockbridge, R. B.; Wolfenden, R. J. Am. Chem. Soc. 2009, 131, 18248
26. Morrow, J. R. Comments Inorg. Chem. 2008, 29, 169
27. Mohamed, M. F.; Neverov, A. A.; Brown, R. S. Inorg. Chem. 2009, 48, 11425
28. Blokzijl, W.; Engberts, J. B. F. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 1545
29. Otto, S.; Engberts, J. B. F. N. Org. Biomol. Chem. 2003, 1, 2809
30. Lee, J. H.; Park, J.; Lah, M. S.; Chin, J.; Hong, J.-I. Org. Lett. 2007, 9, 3729
31. Equation 1 was obtained from the equations for equilibrium binding and for conservation of mass by using the commercially available MAPLE software: Maple 9.00, June 13, 2003, Build ID 13164; Maplesoft, a division of Waterloo Maple Inc.: Waterloo, Ontario, Canada, 1981, - 2003.
32. 2, respectively.
33. Yashiro, M.; Kaneiwa, H.; Oneka, K.; Komiyama, M. Dalton Trans. 2004, 605
34. Drewry, J. A.; Fletcher, S.; Hassan, H.; Gunning, P. T. Org. Biomol. Chem. 2009, 7, 5074
35. Yang, M.-Y.; Iranzo, O.; Richard, J. P.; Morrow, J. R. J. Am. Chem. Soc. 2005, 127, 1064
36. Feng, G.; Mareque-Rivas, J. C.; Torres Martýn de Rosales, R.; Williams, N. H. J. Am. Chem. Soc. 2005, 127, 13470
37. M values in Table 1 are unwarranted.
38. Taft, R. W.; Kamlet, M. J. J. Am. Chem. Soc. 1976, 98, 2886
39. Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877
40. Marcus, Y. J. Solution Chem. 1991, 20, 929
41. Krämer, R. Coord. Chem. Rev. 1999, 182, 243
42. Sträter, N.; Lipscomb, W. N.; Klabunde, T.; Krebs, B. Angew. Chem., Int. Ed. 1996, 35, 2024
43. Gultneh, Y.; Ahvazi, B.; Khan, A. R.; Butcher, R. J.; Tuchagues, J. P. Inorg. Chem. 1995, 34, 3633
44. Hofmann, A.; van Eldik, R. Dalton Trans. 2003, 2979
45. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 10840
46. Zhao, Q.; Liu, S.; Li, Y.; Wang, Q. J. Agric. Food Chem. 2009, 57, 2849
47. 13C NMR and HRMS data are all consistent with the desired compound.
48. Martinho, M.; Banse, F.; Sainton, J.; Philouze, C.; Guillot, R.; Blain, G.; Dorlet, P.; Lecomte, S.; Girerd, J. J. Inorg. Chem. 2007, 46, 1709
49. Gibson, G.; Neverov, A. A.; Brown, R. S. Can. J. Chem. 2003, 81, 495
50. s spH is 8.4.