Kinetic solvent deuterium isotope effect in transesterification of RNA models

Journal of Physical Organic Chemistry

Volumn 18, Issue 5, 2005, Pages 385-397

  Virtanen, Noora ^a   Polari, Lauri ^a   Välilä, Maria ^a   Mikkola, Satu ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

Phosphodiester bonds; RNA; Solvent isotope effect; Transesterification

Indexed keywords

ACETIC ACID; ACETONITRILE; CATALYSTS; DEUTERIUM; ESTERIFICATION; ESTERS; ORGANIC SOLVENTS; REACTION KINETICS; SPECTROPHOTOMETRY;

PHOSPHODIESTER BONDS; PROTON TRANSFER; SOLVENT ISOTOPE EFFECT; TRANSESTERIFICATION;

RNA;

EID: 17444396329     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.883     Document Type: Article

References (71)

1. (a) Gillespie P, Ramirez F, Ugi I, Marquarding D. Angew. Chem. Int. Ed. Engl. 1973; 12: 91-172;
2. (b) Thatcher GRJ, Kluger R. Adv. Phys. Org. Chem. 1989; 25: 99-265;
3. (c) Perreault DM, Anslyn EV. Angew. Chem. Int. Ed Engl. 1997; 36: 432-450;
4. (d) Oivanen M, Kuusela S, Lönnberg H. Chem. Rev. 1998; 98: 961-990;
5. (e) Mikkola S. Kosonen M, Lönnberg H. Curr. Org. Chem. 2002; 6: 523-538.
6. (a) Zhou D, Taira K. Chem. Rev. 1998; 98: 991-1026;
7. (b) Takagi Y, Warashima M, Stech WJ, Yoshinari K, Taira K. Nucleic Acids Res., 2001; 29: 1815-1834;
8. (c) Doherty EA, Doudna JA. Annu. Rev. Biophys. Biomol. Struct. 2001; 30: 457-475;
9. (d) Fedor MJ. Curr. Opin. Struct. Biol. 2002; 12: 289-295;
10. (e) Pyle AM, J. Biol. Inorg. Chem. 2002; 7: 679-690.
11. (a) Trawick BN. Daniher A, Bashkin JK. Chem. Rev. 1998; 98: 939-960;
12. (b) Vlasov W, Śilnikov VN, Zenkova MA. Mol. Biol. 1998; 32: 50-57;
13. (c) Komiyama M, Sumaoka J. Curr. Opin. Chem. Biol., 1998; 2: 751-757.
14. (d) Häner R, Husken D, Hall J. Chimia 2000; 54: 569-573;
15. (e) Covan JA. Curr. Opin. Chem. Biol. 2001; 5: 634-642.
16. Lönnberg H, Strömberg R, Williams A. Org. Biol. Chem. 2004; 2: 2165-2167.
17. (a) Schowen RL. Prog. Phys. Org. Chem. 1972; 9: 275-332;
18. (b) Marnett EM, McKelvey DR. In Solute-Solvent Interactions, Coetzee JF, Ritchie CD (eds). Marcel Dekker: New York, 1969; 343-398;
19. (c) Laughton PM, Robertson RE. In Solute-Solvent Interactions, Coetzee JF, Ritchie CD (eds). Marcel Dekker New York, 1969; 399-538;
20. (d) Kresge AJ, More O'Ferral RA, Powell MF. In Isotopes in Organic Chemistry. Vol. 7. Secondary and Solvent Isotope Effects, Buncel E, Lee CC (eds). Elsevier Amsterdam, 1987; 177-273.
21. (a) Kirby AJ, Younas M. J. Chem. Soc. B 1970; 510-513;
22. (b) Kirby AJ, Younas M. J. Chem. Soc. B 1970; 1165-1172;
23. (c) Usher DA, Richardson DI, Oakenfull DG. J. Am. Chem. Soc. 1970; 92: 4699-4712;
24. (d) Bromilow RH, Khan SA, Kirby AJ. J. Chem. Soc. B 1971; 1091-1097;
25. (e) Williams A, Naylor RA. J. Chem. Soc. B 1971; 1967-1972;
26. (f) Anslyn E, Breslow R. J. Am. Chem. Soc. 1989; 111: 8931-8932;
27. (g) Dalby KN, Kirby AJ, Hollfelder F. J. Chem. Soc. Perkin Trans. 2 1993; 1269-1281;
28. (h) Bruice TC, Blasko A, Arasasingham RD, Kim J. J. Am. Chem. Soc. 1995; 117: 12070-12077;
29. (i) Cassano AG, Anderson VE, Harris ME. J. Am. Chem. Soc. 2002; 124: 10964-10965.
30. (a) Sawata S, Komiyama M, Taira K. J. Am. Chem. Soc. 1995; 117: 2357-2358;
31. (b) Warashima M, Takagi Y, Sawata S, Zhou D, Kuwabara T, Tain K. J. Org. Chem. 1997; 62: 9138-9147;
32. (c) Nakano S, Chadalavada DM, Bevilacqua PC. Science 2000; 287: 1493-1497;
33. (d) Pinard R, Hampel KJ, Heckman JE, Lambert D, Chan PA, Major F, Burke JM. EMBO J. 2001; 20: 6434-6442;
34. (e) Takagi Y, Taira K. J. Am Chem. Soc. 2002; 124: 3850-3852.
35. (a) Deal KA, Hengge AC, Burstyn JN. J. Am. Chem. Soc. 1996; 118: 1713-1718;
36. (b) Komiyama M, Matsumoto Y, Takahashi H, Shiiba T, Tsuzuki H, Yajima H, Sumaoka J. J. Chem. Soc., Perkin Trans. 2 1998; 691-695;
37. (c) Jenkins LA, Bashkin JK, Pennock JD, Florian J, Warshel A. Inorg. Chem. 1999; 38: 3215-3222;
38. (d) Bonfa L, Gatos M, Mancin F, Tecilla P, Tonellato U. Inorg. Chem. 2003; 42: 3943-3949.
39. Davis AM, Hall AD, Williams A. J. Am. Chem. Soc. 1988; 110: 5105-5108.
40. Kosonen M, Yousefi-Salakdeh E, Strömberg R. Lönnberg H. J. Chem. Soc., Perkin Trans. 2 1997; 2661-2666.
41. Oivanen M, Schnell R, Pfleiderer W, Lönnberg H. J. Org. Chem. 1991; 56: 3623-3628.
42. Järvinen P, Oivanen M, Lönnberg H. J. Org. Chem. 1991; 56: 5396-5401.
43. Kosonen M. Yousefi-Salakdeh E, Strömberg R, Lönnberg H. J. Chem. Soc., Perkin Trans. 2 1998; 1589-1595.
44. Oivanen M, Lönnberg H. Acta Chem. Scand. 1991; 45: 968-971.
45. Oivanen M, Lönnberg H, Kazimierczuk Z, Shugar D. Nucleosides Nucleotides 1989; 8: 133-144.
46. Beckmann CH, Kirby AJ, Kuusela S, Tickle DC. J. Chem. Soc., Perkin Trans. 2 1998; 573-581.
47. Mikkola S, Stenman E, Nurmi K, Yousefi-Salakdeh E, Strömberg R, Lönnberg H. J. Chem. Soc., Perkin Trans. 2 1999; 1619-1625.
48. (a) Bunton CA. Shiner VJ Jr. J. Am. Chem. Soc. 1961; 83: 3207-3214;
49. (b) Bender MJ, Pollock EJ, Neveu MC J. Am. Chem. Soc. 1962; 84: 595-599.
50. (a) Philips DR, Fife TF. J. Org. Chem. 1967; 34: 2710-2714;
51. (b) Bencovic SJ, Sampson EJ. J. Am. Chem. Soc. 1971; 93: 4009-4016;
52. (c) DiSabato G, Jencks WP. J. Am. Chem. Soc. 1961; 83: 4400-4405;
53. (d) Milstien S, Fife TF. J. Am. Chem. Soc. 1967; 89: 5820-5825;
54. (e) Bender ML, Lawlor JM. J. Am. Chem. Soc. 1963; 85: 3010-3017;
55. (f) Allen GW, Haake P. J. Am. Chem. Soc. 1973; 95: 8080-8087.
56. Paabo M, Bates RG. J. Phys. Chem. 1970; 74: 706-710.
57. Harned HS, Owen BB. The Physical Chemistry of Electrolytic Solutions (3rd edn). Reinhold: New York, 1958; 752.
58. Covington AK, Robinson RA, Bates RG. J. Phys. Chem. 1966; 70: 3820-3824.
59. Robinson RA, Stokes RH (eds). Electrolyte Solutions (2nd edn). Butterworth: London, 1959; 517-519.
60. Sayer JM, Jencks WP. J. Am. Chem. Soc. 1969; 91: 6353-6361.
61. von Schwartzenbach G, Epprecht A, Erlenmeyer H. Helv. Chin. Acta 1936; 19: 1292-1304.
62. Paabo M, Gates RG, Robinson RA. J. Phys. Chem. 1966; 70: 2073-2077.
63. Harned HS, Owen BB. The Physical Chemistry of Electrolytic Solutions (3rd edn). Reinhold: New York, 1958; 676.
64. Roy RN, Bice J, Greer J, Carlsten JA, Smithson J, Good WS, Moore CP, Roy LN, Kuhler KN. J. Chem. Eng. Data 1997; 42: 41-44.
65. Goldberg RN, Kishore N. Leimen RM. J. Phys. Chem. Ref. Data 2002; 31: 231-370.
66. Kandegedara A, Rorabacher DB. Anal. Chem. 1991; 71: 3140-3144.
67. Fernandez Prini R, Rozenberg de Pattin C, Tanaka K, Bates RG. J. Electroanal. Chem. 1983; 144: 415-422.
68. King EJ. J. Am. Chem. Soc. 1951; 73: 155-159.
69. Bismondo A, Rizzo L, Tomat G, Curto D, di Bernando P, Cassol A. Inorg. Chim. Acta 1983; 74: 21-24.
70. Li NC, Tang P, Mathur R. J. Phys. Chem. 1961; 65: 1074-1076.
71. Laughton PM, Robertson RE. In Solute-Solvent Interactions, Coetzee IF, Ritchie CD (eds). Marcel Dekker: New York, 1969; 412.