Stereocontrolled solid-phase synthesis of phosphorothioate oligoribonucleotides using 2′-O-(2-cyanoethoxymethyl)-nucleoside 3′-O-oxazaphospholidine monomers

Journal of Organic Chemistry

Volumn 77, Issue 18, 2012, Pages 7913-7922

  Nukaga, Yohei ^a   Yamada, Kohei ^b   Ogata, Toshihiko ^a   Oka, Natsuhisa ^c   Wada, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b YAMASA CORPORATION   (Japan)

^c GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING EFFICIENCY; DESTABILIZING EFFECT; DIASTEREO-SELECTIVITY; OLIGORIBONUCLEOTIDES; PHOSPHOROTHIOATES; SOLID PHASE SYNTHESIS;

BIOMOLECULES;

MONOMERS;

2 CYANOETHOXYMETHYL; 2' O (2 CYANOETHOXYMETHYL) NUCLEOSIDE 3' O OXAZAPHOSPHOLIDINE; METHYL GROUP; MONOMER; OLIGONUCLEOTIDE PHOSPHOROTHIOATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COUPLING FACTOR; SOLID PHASE SYNTHESIS; STEREOCHEMISTRY;

MACROMOLECULAR SUBSTANCES; NUCLEOSIDES; OLIGORIBONUCLEOTIDES; OXAZOLES; PHOSPHATES; SOLID-PHASE SYNTHESIS TECHNIQUES; STEREOISOMERISM; THIONUCLEOTIDES;

EID: 84868130699     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301052v     Document Type: Article

References (42)

1. (a) Bumcrot, D.; Manoharan, M.; Koteliansky, V.; Sah, D. W. Y. Nat. Chem. Biol. 2006, 2, 711-719.
2. (b) Shukla, S.; Sumaria, C. S.; Pradeepkumar, P. I. ChemMedChem 2010, 5, 328-349.
3. Seto, A. G. Int. J. Biochem. Cell Biol. 2010, 42, 1298-1305.
4. Echeverri, C. J.; Perrimon, N. Nat. Rev. Genet. 2006, 7, 373-384.
5. (a) Verma, S.; Eckstein, F. Annu. Rev. Biochem. 1998, 67, 99-134.
6. (b) Guga, P.; Koziołkiewicz, M. Chem. Biodiversity 2011, 8, 1642-1681.
7. Oka, N.; Wada, T. Chem. Soc. Rev. 2011, 40, 5829-5843.
8. Frederiksen, J. K.; Piccirilli, J. A. Methods Enzymol. 2009, 468, 289-309.
9. (a) Yano, J.; Ohgi, T.; Ueda, T. Patent WO2006/043521-A1, CAN: 144:450874.
10. (b) Nawrot, B.; Rȩbowska, B.; Michalak, O.; Bulkowski, M.; Błaziak, D.; Guga, P.; Stec, W. J. Pure Appl. Chem. 2008, 80, 1859-1871.
11. (c) Wrzesinski, J.; Wichłacz, A.; Nijakowska, D.; Rebowska, B.; Nawrot, B.; Ciesiołka, J. New J. Chem. 2010, 34, 1018-1026.
12. Matzura, H.; Eckstein, F. Eur. J. Biochem. 1968, 3, 448-452.
13. Sierzchała, A.; Okruszek, A.; Stec, W. J. J. Org. Chem. 1996, 61, 6713-6716.
14. Lesnikowski, Z. J. Nucleosides Nucleotides 1992, 11, 1621-1638.
15. (a) Almer, H.; Stawinski, J.; Strömberg, R. J. Chem. Soc., Chem. Commun. 1994, 1459-1460.
16. (b) Almer, H.; Stawinski, J.; Strömberg, R. Nucleic Acids Res. 1996, 24, 3811-3820.
17. Efimov, V. A.; Molchanova, N. S.; Chakhmakhcheva, O. G. Nucleosides Nucleotides Nucleic Acids 2007, 26, 1087-1093.
18. Oka, N.; Kondo, T.; Fujiwara, S.; Maizuru, Y.; Wada, T. Org. Lett. 2009, 11, 967-970.
19. Somoza, Á. Chem. Soc. Rev. 2008, 37, 2668-2675.
20. (a) Scaringe, S. A.; Wincott, F. E.; Caruthers, M. H. J. Am. Chem. Soc. 1998, 120, 11820-11821.
21. (b) Dellinger, D. J.; Timár, Z.; Myerson, J.; Sierzchala, A. B.; Turner, J.; Ferreira, F.; Kupihár, Z.; Dellinger, G.; Hill, K. W.; Powell, J. A.; Sampson, J. R.; Caruthers, M. H. J. Am. Chem. Soc. 2011, 133, 11540-11556.
22. (c) Umemoto, T.; Wada, T. Tetrahedron Lett. 2004, 45, 9529-9531.
23. (d) Semenyuk, A.; Földesi, A.; Johansson, T.; Estmer-Nilsson, C.; Blomgren, P.; Brännvall, M.; Kirsebom, L. A.; Kwiatkowski, M. J. Am. Chem. Soc. 2006, 128, 12356-12357.
24. (e) Martin, A. R.; Lavergne, T.; Vasseur, J.- J.; Debart, F. Bioorg. Med. Chem. Lett. 2009, 19, 4046-4049.
25. (f) Lavergne, T.; Bertrand, J.-R.; Vasseur, J.-J.; Debart, F. Chem.-Eur. J. 2008, 14, 9135-9138.
26. (g) Saneyoshi, H.; Ando, K.; Seio, K.; Sekine, M. Tetrahedron 2007, 63, 11195-11203.
27. (h) Zhou, C.; Pathmasiri, W.; Honcharenko, D.; Chatterjee, S.; Barman, J.; Chattopadhyaya, J. Can. J. Chem. 2007, 85, 293-301.
28. (i) Lackey, J. G.; Mitra, D.; Somoza, M. M.; Cerrina, F.; Damha, M. J. J. Am. Chem. Soc. 2009, 131, 8496-8502.
29. (j) Cieślak, J.; Grajkowski, A.; Kauffman, J. S.; Duff, R. J.; Beaucage, S. L. J. Org. Chem. 2008, 73, 2774-2783.
30. (a) Ohgi, T.; Masutomi, Y.; Ishiyama, K.; Kitagawa, H.; Shiba, Y.; Yano, J. Org. Lett. 2005, 7, 3477-3480.
31. (b) Shiba, Y.; Masuda, H.; Watanabe, N.; Ego, T.; Takagaki, K.; Ishiyama, K.; Ohgi, T.; Yano, J. Nucleic Acids Res. 2007, 35, 3287-3296.
32. (c) Nagata, S.; Hamasaki, T.; Uetake, K.; Masuda, H.; Takagaki, K.; Oka, N.; Wada, T.; Ohgi, T.; Yano, J. Nucleic Acids Res. 2010, 38, 7845-7857.
33. Oka, N.; Yamamoto, M.; Sato, T.; Wada, T. J. Am. Chem. Soc. 2008, 130, 16031-16037.
34. Ueda, T.; Nagata, S. Patent JP2011-121881A, CAN: 155:68060.
35. (a) Oka, N.; Wada, T.; Saigo, K. J. Am. Chem. Soc. 2002, 124, 4962-4963.
36. (b) Oka, N.; Wada, T.; Saigo, K. J. Am. Chem. Soc. 2003, 125, 8307-8317.
37. Song, Q.; Wang, Z.; Sanghvi, Y. S. Nucleosides Nucleotides Nucleic Acids 2003, 22, 629-633.
38. Hayakawa, Y.; Kawai, R.; Hirata, A.; Sugimoto, J.; Kataoka, M.; Sakakura, A.; Hirose, M.; Noyori, R. J. Am. Chem. Soc. 2001, 123, 8165-8176.
39. (a) Burgers, P. M. J.; Eckstein, F. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 4798-4801.
40. (b) Bryant, F. R.; Benkovic, S. J. Biochemistry 1979, 18, 2825-2829.
41. Potter, B. V. L; Connolly, B. A.; Eckstein, F. Biochemistry 1983, 22, 1369-1377.
42. Griffiths, A. D.; Potter, B. V. L; Eperon, I. C. Nucleic Acids Res. 1987, 15, 4145-4162.