Collect. Czech. Chem. Commun. 2006, 71, 804-819
https://doi.org/10.1135/cccc20060804

Synthesis of Oligoribonucleotides Containing Pyrimidine 2'-O-[(Hydroxyalkoxy)methyl]ribonucleosides

Georgii V. Bobkova, Kirill V. Brilliantova, Sergey N. Mikhailova,*, Jef Rozenskib, Arthur Van Aerschotb and Piet Herdewijnb

a Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov str. 32, Moscow 119991, Russia
b Rega Institute, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium

References

1. Kurreck J.: Eur. J. Biochem. 2003, 270, 1628. <https://doi.org/10.1046/j.1432-1033.2003.03555.x>
2. Sioud M., Iversen P. O.: Curr. Drug Targets 2005, 6, 647. <https://doi.org/10.2174/1389450054863653>
3. Coppelli F. M., Grandis J. R.: Curr. Pharm. Des. 2005, 11, 2825. <https://doi.org/10.2174/1381612054546752>
4. Herdewijn P.: Antisense Nucleic Acid Drug Dev. 2000, 10, 297. <https://doi.org/10.1089/108729000421475>
5. Micklefield J.: Curr. Med. Chem. 2001, 8, 1157. <https://doi.org/10.2174/0929867013372391>
6. Manoharan M.: Biochim. Biophys. Acta 1999, 1489, 117. <https://doi.org/10.1016/S0167-4781(99)00138-4>
7. Freier S. M., Altmann K.-H.: Nucleic Acids Res. 1997, 25, 4429. <https://doi.org/10.1093/nar/25.22.4429>
8. Jin S., Miduturu C. V., McKinney D. C., Silverman S. K.: J. Org. Chem. 2005, 70, 4284. <https://doi.org/10.1021/jo050061l>
9. Das S. R., Fong R., Piccirilli J. A.: Curr. Opin. Chem. Biol. 2005, 9, 585. <https://doi.org/10.1016/j.cbpa.2005.10.009>
10. Zatsepin T. S., Romanova E. A., Oretskaya T. S.: Russ. Chem. Rev. 2004, 73, 701. <https://doi.org/10.1070/RC2004v073n07ABEH000835>
11. Efimtseva E. V., Mikhailov S. N.: Russ. Chem. Rev. 2004, 73, 401. <https://doi.org/10.1070/RC2004v073n04ABEH000847>
12. Nauwelaerts K., Efimtseva E. V., Mikhailov S. N., Herdewijn P. in: Frontiers in Nucleosides and Nucleic Acids (R. F. Schinazi and D. C. Liotta, Eds), p. 187. IHL Press, Tucker, GA, USA 2004.
13. Mikhailov S. N., Efimtseva, E. V., Gurskaya G. V., Zavodnik V. E., De Bruyn A., Janssen G., Rozenski J., Herdewijn P.: J. Carbohydr. Chem. 1997, 16, 75. <https://doi.org/10.1080/07328309708006511>
14. Mikhailov S. N., Rodionov A. A., Efimtseva E. V., Fomitcheva M. V., Padyukova N. Sh., Herdewijn P., Oivanen M.: Carbohydr. Lett. 1997, 2, 321.
15. Mikhailov S. N., Rodionov A. A., Efimtseva E. V., Ermolinsky B. S., Fomitcheva M. V., Padyukova N. Sh., Rothenbacher K., Lescrinier E., Herdewijn P.: Eur. J. Org. Chem. 1998, 2193. <https://doi.org/10.1002/(SICI)1099-0690(199810)1998:10<2193::AID-EJOC2193>3.0.CO;2-3>
16. Mikhailov S. N., Efimtseva E. V.: Collection Symposium Series (Z. Točík and M. Hocek, Eds), Vol. 5, p. 181. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 2002.
17. Efimtseva E. V., Bobkov G. V., Mikhailov S. N., Van Aerschot A., Schepers G., Busson R., Rozenski J., Herdewijn P.: Helv. Chim. Acta 2001, 84, 2387. <https://doi.org/10.1002/1522-2675(20010815)84:8<2387::AID-HLCA2387>3.0.CO;2-F>
18. Senkus M.: J. Am. Chem. Soc. 1946, 68, 734. <https://doi.org/10.1021/ja01209a003>
19. Markiewicz W. T., Wiewiorowski M. in: Nucleic Acid Chemistry. Improved and New Synthetic Procedures and Techniques (L. B. Townsend and R. S. Tipson, Eds), Part 3, p. 229. J. Wiley, New York 1986.
20. Robins M. J., Hansske F., Bermier S. E.: Can. J. Chem. 1981, 59, 3360. <https://doi.org/10.1139/v81-499>
21. Bizdena E., Rozners E., Stromberg R.: Collect. Czech. Chem. Commun. 1996, 61(Special Issue), 283.
22. Boons G. J. P. H., Elie C. J. J., van der Matel G. A., van Boom J. H.: Tetrahedron Lett. 1990, 31, 2197. <https://doi.org/10.1016/0040-4039(90)80107-W>
23. Wincott F. E., Usman N.: Tetrahedron Lett. 1994, 35, 6827. <https://doi.org/10.1016/0040-4039(94)85015-1>
24. Ito T., Ueda S., Takaku H.: J. Org. Chem. 1986, 51, 931. <https://doi.org/10.1021/jo00356a033>
25. Pitsch S., Weiss P. A., Wu X., Ackermann D., Honegger T.: Helv. Chim. Acta 1999, 82, 1753. <https://doi.org/10.1002/(SICI)1522-2675(19991006)82:10<1753::AID-HLCA1753>3.0.CO;2-Y>
26. Pitsch S., Weiss P. A., Jenny L., Stutz A., Wu X.: Helv. Chim. Acta 2001, 84, 3773. <https://doi.org/10.1002/1522-2675(20011219)84:12<3773::AID-HLCA3773>3.0.CO;2-E>
27. Van Aerschot A., Meldgaard M., Schepers G., Volders F., Rozenski J., Busson R., Herdewijn P.: Nucleic Acids Res. 2001, 29, 4187. <https://doi.org/10.1093/nar/29.20.4187>
28. Martin P.: Helv. Chim. Acta 1995, 78, 486. <https://doi.org/10.1002/hlca.19950780219>
29. Tereshko V., Portmann S., Tay E. C., Martin P., Natt F., Altmann K.-H., Egli M.: Biochemistry 1998, 37, 10626. <https://doi.org/10.1021/bi980392a>