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Original Articles

Synthesis of Modified Nucleosides for Incorporation of Formyletheno and Carboxyetheno Adducts of Adenine Nucleosides into Oligonucleotides

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Pages 1203-1206 | Published online: 10 Dec 2007

REFERENCES

  • Iwai , S. 2006 . Nucleosides, Nucleotides and Nucleic Acids , 25 : 561
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  • Pirrung , M. C. , Shuey , S. W. , Lever , D. C. and Fallon , L. 1994 . Bioorg. Med. Chem. Lett. , 4 : 1345
  • Compd. 1 1H NMR (CDCl3): δ 10.04 (CHO, s, 1H), 10.01 (H-5, s, 1H), 8.39 (H-2, s, 1H), 8.27 (H-8, s, 1H), 7.43–7.21 (DMTr, m, 9H), 6.81 (DMTr, dd, J = 4.0 and 9.5 Hz, 4H), 6.58 (H-1′, d, J = 6.4, 1H), 4.77 (H-3′, m, 1H), 4.23 (H-4′, m, 1H), 3.78 (2 × OMe, s, 6H), 3.50 (H-5′, dd, J = 4.7 and 10.2 Hz, 1H), 3.43 (H-5″, dd, J = 5.3 and 10.2 Hz, 1H), 2.88 (H-2′, m, 1H), 2.65 (H-2″, m, 1H); HRMS (FAB) MH+: found 606.2352, calcd for C34H31N5O6 606.2351
  • Trevisiol , E. , Renard , A. , Defrancq , E. and Lhomme , J. 1997 . Tetrahedron Lett. , 38 : 8687
  • Karino , N. , Ueno , Y. and Matsuda , A. 2001 . Nucleic Acids Res. , 29 : 2456
  • Carvalho , V. M. , Gasparutto , D. , Di Maio , P. , Medeiros , M. H.G. and Cadet , J. 2003 . Bioorg. Med. Chem. , 11 : 2445
  • Compd. 2 1H NMR (CDCl3) 7.98 (H-5, s, 1H), 7.83 (H-2, s, 1H), 7.20–7.35 (DMTr, m, 9H), 6.85 (H-8, s, 1H), 6.69-6.77 (DMTr, m, 4H), 6.30 (H-1, dd, J = 8.0 and 5.6 Hz, 1H), 5.35 [-CH(OAc)-CH(OAc)Me, m, 1H], 4.27 [H-3 & -CH(OAc)-CH(OAc)Me, m, 2H), 3.99 (H-4, m, 1H), 3.71 (2 × OMe, s, 6H,), 2.88 (H-5′ & H-5″, m, 2H), 2.51 (H-2′ & H-2″, m, 2H), 2.04 & 2.00 (2 × Ac, s, 2 × 3H), 1.18 (s, 3H, Me)
  • Compd. 3: δ 7.98 (H-5, s, 1H), 7.97 (H-2, s, 1H), 7.20-7.32 (DMTr, m, 9H), 6.95 (H-8, s, 1H), 6.77-6.79 (DMTr, m, 4H), 5.88 (H-1, d, J = 6.0 Hz, 1H), 4.38 (H-2, m, 1H), 3.77 (3 × OMe, s, 9H), 3.72-2.83 (H-3′& H-4′,m, 2H), 3.42-3.46 (H5, dd, J = 13.0 and < 2 Hz, 1H), 3.16-3.20 (H-5, dd, J = 13.0 and < 2 Hz, 1H), 0.72 (C-Me3, s, 6H), 0.51 (C-Me3, s, 3H), −0.08 (Si-Me, s, 6H)
  • Gangjee , A. , Vidwands , A. , Elzein , E. , McGuire , J. J. , Queener , S. F. and Kisliuk , R. L. 2001 . J. Med. Chem. , 44 : 1993

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