Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5267-5270

  Obika, Satoshi ^a   Andoh, Jyun Ichi ^a   Onoda, Mayumi ^a   Nakagawa, Osamu ^a   Hiroto, Akiko ^a   Sugimoto, Tomomi ^a   Imanishi, Takeshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3' AMINO 3' DEOXY 5 METHYL 3' N, 4' C METHYLENEURIDINE; AZETIDINE DERIVATIVE; MONOMER; NUCLEIC ACID; NUCLEOSIDE DERIVATIVE; SUGAR; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL REACTION; DRUG CONFORMATION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 0038684504     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01279-6     Document Type: Article

References (47)

1. Uhlmann E., Peyman A. Chem. Rev. 90:1990;543-584.
2. Beaucage S.L., Iyer R.P. Tetrahedron. 49:1993;6123-6194.
3. Milligan J.F., Matteucci M.D., Martin J.C. J. Med. Chem. 36:1993;1923-1937.
4. Thoung N.T., Hélène C. Angew. Chem., Int. Ed. Engl. 32:1993;666-690.
5. Hashimoto H., Switzer C. J. Am. Chem. Soc. 114:1992;6255-6256.
6. Dougherty J.P., Rizzo C.J., Breslow R. J. Am. Chem. Soc. 114:1992;6254-6255.
7. Giannaris P.A., Damha M.J. Nucleic Acids Res. 21:1993;4742-4749.
8. Alul R., Hoke G.D. Antisense Res. Dev. 5:1995;3-11.
9. Prakash T.P., Jung K.-E., Switzer C. Chem. Commun. 1996;1793-1794.
10. Sheppard T.L., Breslow R. J. Am. Chem. Soc. 118:1996;9810-9811.
11. Kandimalla E.R., Manning A., Zhao Q., Shaw D.R., Byrn R.A., Sasisekharan V., Agrawal S. Nucleic Acids Res. 25:1997;370-378.
12. Schröder H.C., Suhadolnik R.J., Pfleiderer W., Charubala R., Müller W.E.G. Int. J. Biochem. 24:1992;55-63.
13. Wasner M., Suhadolnik R.J., Horvath S.E., Adelson M.E., Kong N., Guan M.-X., Henderson E.E., Pfleiderer W. Helv. Chim. Acta. 80:1997;1061-1072.
14. Kvasyuk E.I., Kulak T.I., Tkachenko U.V., Sentyureva S.L., Mikhaliopulo I.A., Suhadolnik R.J., Henderson E.E., Horvath S.E., Guan M.-X., Pfleiderer W. Helv. Chim. Acta. 81:1998;1278-1284.
15. Gryaznov S.M., Letsinger R.L. Nucleic Acids Res. 20:1992;3403-3409.
16. Gryaznov S.M., Chen J.-K. J. Am. Chem. Soc. 116:1994;3143-3144.
17. Chen J.-K., Schultz R.G., Lloyd D.H., Gryaznov S.M. Nucleic Acids Res. 23:1995;2661-2668.
18. Tereshko V., Gryaznov S.M., Egli M. J. Am. Chem. Soc. 120:1998;269-283.
19. Imanishi T., Obika S. Chem. Commun. 2002;1653-1659.
20. Obika S., Nanbu D., Hari Y., Morio K., In Y., Ishida T., Imanishi T. Tetrahedron Lett. 38:1997;8735-8738.
21. Obika S., Nanbu D., Hari Y., Andoh J., Morio K., Doi T., Imanishi T. Tetrahedron Lett. 39:1998;5401-5404.
22. Obika S., Andoh J., Sugimoto T., Miyashita K., Imanishi T. Tetrahedron Lett. 40:1999;6465-6468.
23. Obika S., Hari Y., Morio K., Imanishi T. Tetrahedron Lett. 41:2000;215-219.
24. Obika S., Hari Y., Morio K., Imanishi T. Tetrahedron Lett. 41:2000;221-224.
25. Obika S., Hari Y., Sugimoto T., Sekiguchi M., Imanishi T. Tetrahedron Lett. 41:2000;8923-8927.
26. Torigoe H., Hari Y., Sekiguchi M., Obika S., Imanishi T. J. Biol. Chem. 276:2001;2354-2360.
27. Obika S., Uneda T., Sugimoto T., Nanbu D., Minami T., Doi T., Imanishi T. Bioorg. Med. Chem. 9:2001;1001-1011 Obika, S.; Hari, Y.; Sekiguchi, M.; Imanishi, T. Angew. Chem., Int. Ed. 2001, 40, 2079-2081; Angew. Chem. 2001, 113, 2149-2151.
28. The 2′,4′-BNA has also been called 'LNA'. See: (a) Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455-456; (b) Wengel, J. Acc. Chem. Res. 1999, 32, 301-310.
29. The 2′,4′-BNA has also been called 'LNA'. See: (a) Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455-456; (b) Wengel, J. Acc. Chem. Res. 1999, 32, 301-310.
30. Obika S., Morio K., Nanbu D., Imanishi T. Chem. Commun. 1997;1643-1644.
31. Obika S., Morio K., Hari Y., Imanishi T. Chem. Commun. 1999;2423-2424.
32. Obika S., Morio K., Hari Y., Imanishi T. Bioorg. Med. Chem. Lett. 9:1999;515-518.
33. Obika S., Morio K., Nanbu D., Hari Y., Itoh H., Imanishi T. Tetrahedron. 58:2002;3039-3049.
34. Davies M.J., Shah A., Bruce I. J. Chem. Soc. Rev. 29:2000;97-107.
35. Asseline U., Thuong N.T., Hélène C. New. J. Chem. 21:1997;5-17.
36. Vlasov V.V., Sil'nikov V.N., Zenkova M.A. Mol. Biol. (Mosc.). 32:1998;50-57.
37. Recently, oligonucleotides N3′→P5′ phosphoramidate with a conformationally restricted or locked sugar moiety have been demonstrated; see: (a) Wang, G.; Stoisavljevic, V. Nucleosides Nucleotides Nucleic Acids 2000, 19, 1413-1425; (b) Kværnø, L.; Wightman, R. H.; Wengel, J. J. Org. Chem. 2001, 66, 5106-5112; (c) Obika, S.; Onoda, M.; Morita, K.; Andoh, J.; Koizumi, M.; Imanishi, T. Chem. Commun. 2001, 1992-1993.
38. Recently, oligonucleotides N3′→P5′ phosphoramidate with a conformationally restricted or locked sugar moiety have been demonstrated; see: (a) Wang, G.; Stoisavljevic, V. Nucleosides Nucleotides Nucleic Acids 2000, 19, 1413-1425; (b) Kværnø, L.; Wightman, R. H.; Wengel, J. J. Org. Chem. 2001, 66, 5106-5112; (c) Obika, S.; Onoda, M.; Morita, K.; Andoh, J.; Koizumi, M.; Imanishi, T. Chem. Commun. 2001, 1992-1993.
39. Recently, oligonucleotides N3′→P5′ phosphoramidate with a conformationally restricted or locked sugar moiety have been demonstrated; see: (a) Wang, G.; Stoisavljevic, V. Nucleosides Nucleotides Nucleic Acids 2000, 19, 1413-1425; (b) Kværnø, L.; Wightman, R. H.; Wengel, J. J. Org. Chem. 2001, 66, 5106-5112; (c) Obika, S.; Onoda, M.; Morita, K.; Andoh, J.; Koizumi, M.; Imanishi, T. Chem. Commun. 2001, 1992-1993.
40. Staudinger H., Meyer M. Helv. Chim. Acta. 2:1919;619-635.
41. A Staudinger reaction of 1-azido-2,3-diols was performed to give the corresponding aziridines as main products and azetidines as minor products. See: (a) Coldham, I.; Collis, A. J.; Mould, R. J.; Rathmell, R. E. J. Chem. Soc., Perkin Trans. 1 1995, 2739-2745; (b) Marples, B. A.; Toon, R. C. Tetrahedron Lett. 1999, 40, 4873-4876.
42. A Staudinger reaction of 1-azido-2,3-diols was performed to give the corresponding aziridines as main products and azetidines as minor products. See: (a) Coldham, I.; Collis, A. J.; Mould, R. J.; Rathmell, R. E. J. Chem. Soc., Perkin Trans. 1 1995, 2739-2745; (b) Marples, B. A.; Toon, R. C. Tetrahedron Lett. 1999, 40, 4873-4876.
43. 2O (+5% DCl), respectively.
44. 1′2′-1)/6.9. See: (a) Ref. 13; (b) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333-2344; (c) Altona, C. Recl. Trav. Chim. Pays-Bas 1982, 101, 413-433; (d) De Leeuw, F. A. A. M.; Altona, C. J. Chem. Soc., Perkin Trans. 2 1982, 375-384.
45. 1′2′-1)/6.9. See: (a) Ref. 13; (b) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333-2344; (c) Altona, C. Recl. Trav. Chim. Pays-Bas 1982, 101, 413-433; (d) De Leeuw, F. A. A. M.; Altona, C. J. Chem. Soc., Perkin Trans. 2 1982, 375-384.
46. 1′2′-1)/6.9. See: (a) Ref. 13; (b) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333-2344; (c) Altona, C. Recl. Trav. Chim. Pays-Bas 1982, 101, 413-433; (d) De Leeuw, F. A. A. M.; Altona, C. J. Chem. Soc., Perkin Trans. 2 1982, 375-384.
47. max value. Numerical calculations were performed on an Octane™ (SGI) workstation.