Facile and efficient approach for the synthesis of N2-dimethylaminomethylene-2′-O-methylguanosine

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 1, 2010, Pages 129-131

  Mukobata, Tsuyoshi ^a   Ochi, Yosuke ^a   Ito, Yuji ^a   Wada, Shun ichi ^a   Urata, Hidehito ^a  

^a OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

2 Hydroxyl group; 2 O Methylguanosine; Guanosine; Methylation; Triisopropylbenzenesulfonyl group

Indexed keywords

BENZENE DERIVATIVE; BUTANOL; GUANOSINE; GUANOSINE DERIVATIVE; N 2 DIMETHYLAMINOMETHYLENE 2' O METHYLGUANOSINE; OLIGONUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CONTROLLED STUDY; METHYLATION; PURIFICATION; SYNTHESIS;

GUANOSINE; HYDROCARBONS, IODINATED; METHYLATION; SODIUM COMPOUNDS;

EID: 72049090612     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.11.016     Document Type: Article

References (22)

1. Inoue H., Hayase Y., Asaka M., Imura A., Iwai S., Miura K., and Ohtsuka E. Nucleic Acids Res. Symp. Ser. 16 (1985) 165-168
2. Inoue H., Hayase Y., Imura A., Iwai S., Miura K., and Ohtsuka E. Nucleic Acids Res. 15 (1987) 6131-6148
3. Sproat B.S., Lamond A.I., Beijer B., Neuner P., and Ryder U. Nucleic Acids Res. 9 (1989) 3373-3386
4. Uhlmann E., and Peyman A. Chem. Rev. 90 (1990) 543-584
5. Allerson C.R., Sioufi N., Jarres R., Prakash T.P., Naik N., Berdeja A., Wanders L., Griffey R.H., Swayze E.E., and Bhat B. J. Med. Chem. 48 (2005) 901-904
6. Kraynack B.A., and Baker B.F. RNA 12 (2006) 163-176
7. Leonard T.E., Bhan P., and Miller P.S. Nucleosides Nucleotides 11 (1992) 1201-1204
8. Robins M.J., Naik S.R., and Lee A.S.K. J. Org. Chem. 39 (1974) 1891-1899
9. Chow S., Wen K., Sanghvi Y.S., and Theodorakis E.A. Bioorg. Med. Chem. Lett. 13 (2003) 1631-1634
10. Chow S., Wen K., Sanghvi Y.S., and Theodorakis E.A. Nucleosides Nucleotides 22 (2003) 583-587
11. Beigelman L., Haeberli P., Sweedler D., and Karpeisky A. Tetrahedron 56 (2000) 1047-1056
12. Kore A.R., Parmar G., and Reddy S. Nucleosides Nucleotides, Nucleic Acids 25 (2006) 307-314
13. Sproat B.S., Beijer B., and Iribarren A. Nucleic Acids Res. 18 (1990) 41-49
14. Grotli M., Douglas M., Beijer B., Garcia R.G., Eritja R., and Sproat B. J. Chem. Soc., Perkin Trans. 1 (1997) 2779-2788
15. Wagner E., Oberhauser B., Holzner A., Brunar H., Issakides G., Schaffner G., Cotten M., Knollmuller M., and Neo C.R. Nucleic Acids Res. 19 (1991) 5965-5971
16. Grotli M., Douglas M., Beijer B., Eritja R., and Sproat B. Bioorg. Med. Chem. Lett. 7 (1997) 425-428
17. Zlatev I., Vasseur J.J., and Morvan F. Tetrahedron 63 (2007) 11174-11178
18. Daskalov H.P., Sekine M., and Hata T. Tetrahedron Lett. 21 (1980) 3899-3902
19. Saneyoshi H., Seio K., and Sekine M. J. Org. Chem. 70 (2005) 10453-10460
20. macromodel, Version 9.1; Schrodinger, L.L.C.: Portland, OR, 2006.
21. McBride L.J., Kierzek R., Beaucage S.L., and Caruthers M.H. J. Am. Chem. Soc. 108 (1986) 2040-2048
22. The spectroscopic data were in good agreement with previously published data; Ref. 14.