Preparation and properties of 2',5'-linked oligonucleotide analogues containing 3'-O,4'-C-methyleneribonucleosides

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 4, 1999, Pages 515-518

  Obika, Satoshi ^a   Morio, Ken ichiro ^a   Hari, Yoshiyuki ^a   Imanishi, Takeshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

DNA; Nucleic acids; Nucleosides; Nucleotides

Indexed keywords

OLIGONUCLEOTIDE; RIBONUCLEOSIDE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; REACTION ANALYSIS; SYNTHESIS;

BASE SEQUENCE; KINETICS; OLIGONUCLEOTIDES; RIBONUCLEOSIDES;

EID: 0033593864     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00028-1     Document Type: Article

References (25)

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15. 15. In recent years, various kinds of conformationally restricted (or fixed) nucleosides (or nucleotides) were prepared and their properties were reported: Herdewijn, P. Liebigs Ann. Chem. 1996, 1337 and references cited therein; Zou, R.; Matteucci, M. D. Tetraahedron Lett. 1996, 37, 941; Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735; Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401; Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455; Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J. Tetrahedron 1998, 54, 3607.
16. 15. In recent years, various kinds of conformationally restricted (or fixed) nucleosides (or nucleotides) were prepared and their properties were reported: Herdewijn, P. Liebigs Ann. Chem. 1996, 1337 and references cited therein; Zou, R.; Matteucci, M. D. Tetraahedron Lett. 1996, 37, 941; Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735; Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401; Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455; Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J. Tetrahedron 1998, 54, 3607.
17. 15. In recent years, various kinds of conformationally restricted (or fixed) nucleosides (or nucleotides) were prepared and their properties were reported: Herdewijn, P. Liebigs Ann. Chem. 1996, 1337 and references cited therein; Zou, R.; Matteucci, M. D. Tetraahedron Lett. 1996, 37, 941; Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735; Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401; Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455; Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J. Tetrahedron 1998, 54, 3607.
18. 15. In recent years, various kinds of conformationally restricted (or fixed) nucleosides (or nucleotides) were prepared and their properties were reported: Herdewijn, P. Liebigs Ann. Chem. 1996, 1337 and references cited therein; Zou, R.; Matteucci, M. D. Tetraahedron Lett. 1996, 37, 941; Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735; Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401; Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455; Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J. Tetrahedron 1998, 54, 3607.
19. 15. In recent years, various kinds of conformationally restricted (or fixed) nucleosides (or nucleotides) were prepared and their properties were reported: Herdewijn, P. Liebigs Ann. Chem. 1996, 1337 and references cited therein; Zou, R.; Matteucci, M. D. Tetraahedron Lett. 1996, 37, 941; Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735; Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401; Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455; Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J. Tetrahedron 1998, 54, 3607.
20. 15. In recent years, various kinds of conformationally restricted (or fixed) nucleosides (or nucleotides) were prepared and their properties were reported: Herdewijn, P. Liebigs Ann. Chem. 1996, 1337 and references cited therein; Zou, R.; Matteucci, M. D. Tetraahedron Lett. 1996, 37, 941; Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735; Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401; Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455; Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J. Tetrahedron 1998, 54, 3607.
21. 16. The synthesis of 5′-O-dimethoxytrityl-3′,O-4,C-methylene-5-methyluridine (2b) will be reported elsewhere.
22. 17. Sinha, N. D.; Cook, R. M. Nucleic Acids Res. 1988, 16, 2659.
23. 18. The oligonucleotides were synthesized on DNA synthesizer (Gene Assembler® Plus, Pharmacia, 0.2 μmol scale, 5′-dimethoxytrityl on). After cleavage from the support and deprotection with conc. ammonia at 70 °C for 3 h, removal of the 5′-O-dimethoxytrityl group and purification of the oligonucleotides were performed on NENSORB ™ PREP reverse-phase columns. The purity of these oligonucleotides was verified using analytical HPLC and the composition was determined by MALDI-TOF-mass spectrometry. UV-Spectroscopically determined yields after chromatographic purification were in the range of 6-40%.
24. 19. From the Tm measurements targeting mismatched DNA sequences, recognition by the modified oligonucleotides containing 1 was found to be sequence selective. For example, the Tm value of the modified oligonucleotide 5a towards its mismatched sequence, 5′-d(AGCAAATAACGC)-3′ 19, was 33 °C, while that of the unmodified oligonucleotide 15 towards 19 was 37 °C.
25. 20. Kool, E. T. Chem. Rev. 1997, 97, 1473.