A transition state analog for phosphate diester cleavage catalyzed by a small enzyme-like metal ion complex

Bioorganic Chemistry

Volumn 35, Issue 5, 2007, Pages 366-374

  Yang, Meng Yin ^a   Morrow, Janet R ^a   Richard, John P ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

Metal ion catalysis; Phosphate diester; RNA analog

Indexed keywords

METAL ION; ORGANOPHOSPHATE; TRANSITION ELEMENT;

ARTICLE; BINDING AFFINITY; BINDING SITE; CATALYSIS; CHEMICAL STRUCTURE; PRIORITY JOURNAL; STATISTICAL SIGNIFICANCE;

ANIONS; BIOCHEMISTRY; CATALYSIS; CHEMISTRY, ORGANIC; HYDROGEN-ION CONCENTRATION; IONS; KINETICS; METALS; MODELS, CHEMICAL; MODELS, STATISTICAL; PHOSPHATES; PROTEIN BINDING; RNA; SUBSTRATE SPECIFICITY;

EID: 34548118293     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2007.02.003     Document Type: Article

References (35)

1. Jencks W.P. Catalysis in Chemistry and Enzymology (1987), Dover Publications, New York
2. Hartwell E., Hodgson D.R.W., and Kirby A.J. J. Am. Chem. Soc. 122 (2000) 9326-9327
3. Jencks W.P. Acc. Chem. Res. 9 (1976) 425-432
4. Rios A., Amyes T.L., and Richard J.P. J. Am. Chem. Soc. 122 (2000) 9373-9385
5. Richard J.P., and Jencks W.P. J. Am. Chem. Soc. 106 (1984) 1396-1401
6. Washabaugh M.W., and Jencks W.P. J. Am. Chem. Soc. 111 (1989) 683-692
7. Jencks W.P., Brant S.R., Gandler J.R., Fendrich G., and Nakamura C. J. Am. Chem. Soc. 104 (1982) 7045-7051
8. Kresge A.J. Chem. Soc. Rev. 2 (1973) 475-503
9. Crugeiras J., and Richard J.P. J. Am. Chem. Soc. 126 (2004) 5164-5173
10. Lienhard G.E. Science 180 (1973) 149-154
11. Wolfenden R. Nature 223 (1969) 704-705
12. Pauling L. Nature 161 (1948) 707-709
13. Iranzo O., Elmer T., Richard J.P., and Morrow J.R. Inorg. Chem. 42 (2003) 7737-7746
14. Iranzo O., Kovalevsky A.Y., Morrow J.R., and Richard J.P. J. Am. Chem. Soc. 125 (2003) 1988-1993
15. Yang M.-Y., Iranzo O., Richard J.P., and Morrow J.R. J. Am. Chem. Soc. 127 (2005) 1064-1065
16. O'Donoghue A., Pyun S.Y., Yang M.-Y., Morrow J.R., and Richard J.P. J. Am. Chem. Soc. 128 (2006) 1615-1621
17. Atkins T.J., Richman J.E., and Oettle W.F. Org. Syn. 58 (1978) 86-98
18. Brown D.M., and Usher D.A. J. Chem. Soc. (1965) 6558-6564
19. Jencks W.P., and Regenstein J. In: Fasman G.D. (Ed). Handbook of Biochemistry and Molecular Biology, Physical and Chemical Data. Third Ed. vol. 1 (1976), CRC Press, Cleveland, OH 305-351
20. Feng G., Mareque-Rivas J.C., Martin de Rossales R.T., and Williams N.H. J. Am. Chem. Soc. 128 (2005) 13470-13471
21. Footnote 10 of Ref. [16].
22. Iranzo O., Richard J.P., and Morrow J.R. Inorg. Chem. 43 (2004) 1743-1750
23. Yang M.-Y., Richard J.P., and Morrow J.R. Chem. Commun. (2003) 2832-2833
24. Bernasconi C.F. Pure Appl. Chem. 54 (1982) 2335-2348
25. Bernasconi C.F. Acc. Chem. Res. 25 (1992) 9-16
26. Jencks W.P. Adv. Enzymol. Relat. Areas Mol. Biol. 43 (1975) 219-410
27. Cannon W.R., and Benkovic S.J. J. Biol. Chem. 273 (1998) 26257-26260
28. Warshel A. J. Biol. Chem. 273 (1998) 27035-27038
29. Feng G., Mareque-Rivas J.C., and Williams N.H. Chem. Commun. (2006) 1845-1847
30. Babbitt P.C., Hasson M.S., Wedekind J.E., Palmer D.R.J., Barrett W.C., Reed G.H., Rayment I., Ringe D., Kenyon G.L., and Gerlt J.A. Biochemistry 35 (1996) 16489-16501
31. Zhang X., and Houk K.N. Acc. Chem. Res. 38 (2005) 379-385
32. Kraut A., and Yamada E.W. J. Biol. Chem. 246 (1971) 2021-2030
33. Jencks W.P. Proc. Natl. Acad. Sci. USA 78 (1981) 4046-4050
34. Amyes T.L., O'Donoghue A.C., and Richard J.P. J. Am. Chem. Soc. 123 (2001) 11325-11326
35. Amyes T.L., Richard J.P., and Tait J.J. J. Am. Chem. Soc. 127 (2005) 15708-15709