Synthesis of 1-(2′-O-methyl-β-D-ribofuranosyl)-5-nitroindole and its phosphoramidite derivative

Tetrahedron Letters

Volumn 45, Issue 29, 2004, Pages 5629-5632

  Gaubert, Gilles ^a   Wengel, Jesper ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

2 O Me RNA Monomer; 5 Nitroindole ribonucleoside; Phosphoramidite synthesis; Universal base; Universal hybridization

Indexed keywords

1 (2' O METHYL BETA DEXTRO RIBOFURANOSYL) 5 NITROINDOLE; INDOLE DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AUTOMATION; CHEMICAL ANALYSIS; DIASTEREOISOMER; SYNTHESIS;

EID: 3042665560     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.116     Document Type: Article

References (23)

1. Othsuka E., Matsuki S., Ikehara M., Takahashi Y., Matsubara K. J. Biol. Chem. 260:1985;2605-2608
2. Takahashi Y., Kato K., Hayashizaki Y., Wakabayashi T., Ohtsuka E., Matsuki S., Ikehara M., Matsubara K. Proc. Natl. Acad. Sci. U.S.A. 82:1985;1931-1935
3. Liu H., Nichols R. Biotechniques. 16:1994;24-26
4. Kamaya H., Sakaguchi T., Murata N., Fujimuro M., Miura H., Ishikawa K., Shimizu M., Inoue H., Nishimura S., Matsukage A., Masutani C., Hanaoka F., Ohtsuka E. Chem. Pharm. Bull. 40:1992;2792-2795
5. Martin F.H., Castro M.M., Aboul-ela F., Tinoco I. Nucleic Acids Res. 13:1985;8927-8938
6. Van Aerschot A., Peeters B., Van Derhaegue H. Nucleosides Nucleotides. 6:1987;437-439
7. Kawase Y., Iwai S., Inoue H., Miura K., Ohtsuka E. Nucleic Acids Res. 14:1986;7727-7736
8. Loakes D. Nucleic Acids Res. 29:2001;2437-2447
9. Loakes D., Brown D.M. Nucleic Acids Res. 22:1994;4039-4043
10. Inoue H., Hayase Y., Imura A., Iwai S., Miura K., Ohtsuka E. Nucleic Acids Res. 15:1987;6131-6148
11. Lesnik E.A., Guinosso C.J., Kawasaki A.M., Sasmor H., Zounes M., Cummins L.L., Ecker D.J., Cook P.D., Freier S.M. Biochemistry. 32:1993;7832-7838
12. Blommers M.J.J., Pieles U., De Mesmaeker A. Nucleic Acids Res. 22:1994;4187-4194
13. Mukhanov V.I., Miniker T.D., Preobrazhenskaya M.N. Zh. Org. Khim. 13:1977;214-218
14. Ramasamy K., Robins R.K., Revankar G.R. J. Heterocycl. Chem. 24:1987;863-868
15. Cristalli G., Franchetti P., Grifantini M., Nocentini G., Vittori S. J. Med. Chem. 32:1989;1463-1466
16. + calcd: 359.0849; found 359.0848
17. Kane P.D., Mann J. J. Chem. Soc., Perkin Trans. 1. 1984;657-660
18. Wilcox C.S., Otoski R.M. Tetrahedron Lett. 27:1986;1011-1014
19. 12
20. Gotfredsen C.H., Jacobsen J.P., Wengel J. Bioorg. Med. Chem. 4:1996;1217-1225
21. + calcd: 573.2428; found: 573.2420. Key results of NOE experiments: irradiation of H-3′ gives 7.3% enhancement of the H-2′ signal and 3.1% of the H-6 signal. Irradiation of H-6 gives 2.9% enhancement of the H-3′ signal and 1.4% of the H-2′ signal
22. +: calcd: 331.0901; found: 331.0905
23. 6, 121.5 MHz) δ 151.4, 150.9