Acidity of secondary hydroxyls in ATP and adenosine analogues and the question of a 2′,3′-hydrogen bond in ribonucleosides

Journal of the American Chemical Society

Volumn 126, Issue 45, 2004, Pages 14710-14711

  Åström, Hans ^a   Limén, Ethel ^a   Strömberg, Roger ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DERIVATIVE; ADENOSINE TRIPHOSPHATE DERIVATIVE; DIMETHYL SULFOXIDE; HYDROGEN; HYDROXYL GROUP; METHANOL; OXYGEN; RIBONUCLEOSIDE;

ACIDITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; HYDROGEN BOND; PH;

ADENOSINE; ADENOSINE TRIPHOSPHATE; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; KINETICS; RIBONUCLEOSIDES;

EID: 8844250755     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0477468     Document Type: Article

References (26)

1. Verma, S.; Eckstein, F. Annu. Rev. Biochem. 1998, 67, 99-134.
2. (b) Verma, S.; Vaish, N. K.; Eckstein, F. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Eds.; Eisevier: New York, 1999; Vol. 6. pp 217-233.
3. (c) Warashina, M.; Takagi, Y.; Stec, W. J.; Taira, K. Curr. Opin. Biotechnol 2000, 11, 354-362.
4. Herschlag, D.; Eckstein, F.; Cech, T. R. Biochemistry 1993, 32, 8299-8311.
5. (b) Cech, T. R.; Herschlag, D. In Nucleic Acids and Molecular Biology; Eckstein, F., Lilley, D. M. J., Eds.; Springer-Verlag: New York, 1996; Vol. 10, pp 1-17.
6. (c) Strobel, S. A. Curr. Opin. Biotechnol. 1999, 9, 346-352.
7. (d) Yoshida, A.; Shan, S.; Herschlag, D.; Piccirilli, J. A. Chem. Biol. 2000, 7, 85-96.
8. (e) Sjögren, A.-S.; Strömberg, R.; Sjöberg, B.-M. Nucleic Acids Res. 1997, 25, 3543-3549.
9. (f) Gordon, P. M.; Fong, R.; Deb, S. K.; Li, N.-S.; Schwans, J. P.; Ye, J.-D.; Piccirilli, J. A. Chem. Biol. 2004, 11, 237-246.
10. Herschlag, D.; Eckstein, F.; Cech, T. R. Biochemistry 1993, 32, 8312-8321.
11. Johnson, R. W.; Marschner, T. M.; Oppenheimer N. J. J. Am. Chem. Soc. 1988, 110, 2257-2263.
12. Velikyan, I.; Acharya, S.; Trifonova, A.; Foeldesi, A.; Chattopadhyaya, J. J. Am. Chem. Soc. 2001, 123, 2893-2894.
13. Lyne, P. D.; Karplus, M. J. Am. Chem. Soc. 2000, 122, 166-167.
14. (b) Roussev, C. D.; Ivanova, G. D.; Bratovanova, E. K.; Vassilev, N. G.; Petkov, D. D. J. Am. Chem. Soc. 1999, 121, 11267-11272.
15. Strobel, S. A.; Ortoleva-Donnelly, L. Chem. Biol. 1999, 6, 153-165.
16. (b) Gordon, P. M.; Sontheimer, E. J.; Piccirilli, J. A. Biochemistry 2000, 39, 12939-12952.
17. Pitha, J. Biochemistry 1970, 9, 3678-3682.
18. (b) Acharya, P.; Chattopadhyaya, J. J. Org. Chem. 2002, 67, 1852-1865.
19. Mullay, J. J. Am. Chem. Soc. 1985, 107, 7271-7275.
20. Darzynkiewicz, E.; Sierakowski, H.; Shugar, D. Z. Naturforsch., C 1975, 30, 565-570.
21. Shan, S.; Herschlag, D. J. Am. Chem. Soc. 1996, 118, 5515-5518.
22. (b) Shan, S.; Herschlag, D. Proc. Natl. Acad Sci. U.S.A. 1996, 93, 14474-14479.
23. Schwanz, B.; Drueckhammer, D. G. J. Am. Chem. Soc. 1995, 117, 11902-11905.
24. Inamoto, N.; Masuda, S. Tetrahedron Lett. 1977, 3287.
25. (b) Inamoto, N.; Masuda, S.; Tori, K.; Yoshimura, Y. Tetrahedron Lett. 1978, 4547.
26. (c) Inamoto, N.; Masuda, S. Chem. Lett. 1982, 1003, 1007.