Efficient synthesis of [2′-18O]uridine and its incorporation into oligonucleotides: A new tool for mechanistic study of nucleotidyl transfer reactions by isotope effect analysis

Journal of Organic Chemistry

Volumn 73, Issue 1, 2008, Pages 309-311

  Dai, Qing ^a   Frederiksen, John K ^a   Anderson, Vernon E ^b   Harris, Michael E ^b   Piccirilli, Joseph A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

^b CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOTOPE EFFECTS; NUCLEOTIDYL HYDROLASES; NUCLEOTIDYL TRANSFER REACTIONS; REGIOSELECTIVE OPENINGS;

ENZYME ACTIVITY; ISOTOPES; MOLECULAR MECHANICS; NUCLEIC ACIDS; REGIOSELECTIVITY; SOLID STATE REACTIONS;

OLIGONUCLEOTIDES;

BENZOIC ACID; CYCLOURIDINE; OLIGONUCLEOTIDE; OXYGEN 18; PHOSPHORAMIDOUS ACID; POTASSIUM; RNA; UNCLASSIFIED DRUG; URIDINE;

ARTICLE; CHEMICAL REACTION; ISOTOPE ANALYSIS; ISOTOPE LABELING; ONE POT SYNTHESIS; REACTION ANALYSIS;

NUCLEIC ACID CONFORMATION; NUCLEOTIDES; OLIGONUCLEOTIDES; OXYGEN ISOTOPES; STEREOISOMERISM; URIDINE;

EID: 37549011321     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701727h     Document Type: Article

References (41)

1. Oivanen, M.; Kuusela, S.; Lonnberg, H. Chem. Rev. 1998, 98, 961.
2. (a) Northrop, D. B. Methods 2001, 24, 117.
3. (b) Hengge, A. C. FEBS Lett. 2001, 501, 99.
4. Anderson, V. E.; Ruszczycky, M. W.; Harris, M. E. Chem. Rev. 2006, 106, 3236.
5. (a) Follman, H.; Hogencamp, H. P. C. J. Am. Chem. Soc. 1970, 92, 671.
6. (b) Solsten, R. T.; McCloskey, J. A.; Schram, K. H. Nucleosides Nucleotides 1982, 1, 57.
7. (c) Schubert, E. M.; Schram, K. H. J. Labelled Compd. Radiopharm. 1982, 19, 929.
8. (d) Schwartz, H. M.; MacCoss, M.; Danyluk, S. S. J. Am. Chem. Soc. 1983, 105, 5901.
9. (e) Schwartz, H. M.; MacCoss, M.; Danyluk, S. S. Magn. Reson. Chem. 1985, 23, 885.
10. Pang, H.; Schram, K. H.; Smith, D. L.; Gupta, S. P.; Townsend, L. B.; McCloskey, J. A. J. Org. Chem. 1982, 47, 3923.
11. Wnuk, S. F.; Chowdhury, S. M.; Garcia, P. I., Jr.; Robins, M. J. J. Org. Chem. 2002, 67, 1816.
12. (a) Jiang, C.; Suhadolnik, R. J.; Baker, D. C. Nucleosides Nucleotides 1988, 7, 271.
13. (b) D'Souza, F. W.; Lowary, T. L. J. Org. Chem. 1998, 63, 3166.
14. Ueda, T. Synthesis and Reaction of Pyrimidine Nucleosides. In Chemistry of Nucleosides and Nucleotides, 1st ed.; Townsend L. B., Ed.; Plenum Press: New York and London, 1988; pp 1-112.
15. Sebesta, D. P.; O' Rourke, S. S.; Martinez, R. L.; Pieken, W. A.; McGee, D. P. C. Tetrahedron 1996, 52, 14385.
16. Shriver, D. F.; Atkins, P. W.; Salvador, P. Inorganic Chemistry, 3rd ed.; W. H. Freeman: New York, 2006.
17. Roy, S. K.; Tang, J.-Y. Org. Process Res. Dev. 2000, 4, 170.
18. Ross, B. S.; Springer, R. H.; Tortorici, Z.; Dimock, S. Nucleosides Nucleotides 1997, 16, 1641.
19. (a) Delia, T. J.; Beranek, J. J. Carbohydr., Nucleosides Nucleotides 1977, 4, 349.
20. (b) Ozaki, H.; Nakajima, K.; Tatsui, K.; Izumi, C.; Kuwahara, M.; Sawai, H. Bioorg. Med. Chem. Lett. 2003, 13, 2441.
21. (a) Li, H.; Jiang, Z.; Wang, X.; Zheng, C. Synth. Commun. 2006, 36, 1933.
22. (b) Vasil'eva, S. V.; Abramova, T. V. Sil'nikov, V. N. Russ. J. Bioorg. Chem. 2004, 30, 264.
23. Sekiya Takao Ukita, T. Chem. Pharm. Bull. 1967, 15, 1498.
24. Divakar, K. J.; Reese, C. B. J. Chem. Soc., Perkin Trans. 1 1982, 1625.
25. Imazawa, M.; Ueda, T.; Ukita, T. Chem. Pharm. Bull. 1975, 23, 604.
26. Ozaki, H.; Nakajima, K.; Tatsui, K.; Izumi, C.; Kuwahara, M.; Sawai, H. Bioorg. Med. Chem. Lett. 2003, 13, 2441.
27. Codington, J. F.; Doerr, I.; Van Praag, D.; Bendich, A.; Fox, J. J. J. Am. Chem. Soc. 1961, 83, 5030.
28. Vanheusden, V.; Munier-Lehmann, H.; Pochet, S.; Herdewijn, P.; Van Calenbergh, S. Bioorg. Med. Chem. Lett. 2002, 12, 2695.
29. Aoyama, Y.; Sekine, T.; Iwamoto, Y.; Kawashima, E.; Ishido, Y. Nucleosides Nucleotides 1996, 15, 733.
30. Sukeda, M.; Shuto, S.; Sugimoto, I.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 8988.
31. a = 4.8).
32. This reactivity trend should be viewed with caution, as it is based on a limited number of independent examples rather than systematic investigation of factors such as solvent, pH, temperature, bases, and the "chemical context" of the nucleophilic atom.
33. In the presence of 2 equiv of BzOH (without KOBz), the reaction produced only a trace amount of product as indicated by TLC, presumably due to the weak nucleophilicity of benzoic acid.
34. Risley, J. M.; Van Etten, R. L. J. Am. Chem. Soc. 1979, 101, 252.
35. (a) Hakimelahi, G. H.; Proba, Z. A.; Ogilvie, K. K. Tetrahedron Lett. 1981, 22, 4775.
36. (b) Moyroud, E.; Biala, E.; Strazewski, P. Tetrahedron 2000, 56, 1475.
37. (c) Milecki, J.; Zamaratski, E.; Maltseva, T. V.; Foldesi, A.; Adamiak, R. W.; Chattopadhyaya, J. Tetrahedron 1999, 55, 6603.
38. For conversion of uridine to cytidine, see: (a) Saladino, R.; Crestini, C.; Bernini, R.; Frachey, G.; Mincione, E.; J. Chem. Soc., Perkin Trans. 1 1994, 21, 3053.
39. For conversion of uridine to adenosine, see: (b) Trelles, J. A.; Valino, A. L.; Runza, V.; Lewkowicz, E. S.; Iribarren, A. M., Biotechnol. Lett. 2005, 27, 759.
40. (c) Trelles, J. A.; Fernandez, M.; Lewkowicz, E. S.; Iribarren, A. M.; Sinisterra, J. V.; Tetrahedron Lett. 2003, 44, 2605.
41. For conversion of uridine to guanosine, see: (d) Mikami, Y.; Matsumoto, S.; Hayashi, Y.; Sato, T. Jpn. Kokai Tokkyo Koho, JP 2001269192 A, 2001.