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III. OLIGONUCLEOTIDES: Chemistry

Phosphitylation of Primary Carboxamides. Synthesis of Peptide-Oligonucleotide Conjugates with Acylphosphoramidate Linkages

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Pages 825-828 | Published online: 16 Feb 2007

References

  • Nielsen , J. , Taagard , M. , Marugg , J. , van Boom , J. H. and Dahl , O. 1986 . Nucleic Acids Res. , 14 : 7391 – 7403 .
  • Sinha , N. D. , Biernat , J. , McManus , J. and Köster , H. 1984 . Nucleic Acids Res. , 12 : 4539 – 4557 .
  • N-acylphosphoramidate 3 is stable to: 0.05 M K2CO3 in MeOH/dioxane 1:1, 24 h, r.t.; 0.25 M LiOH in MeOH/dioxane/H2O 1.5:1.5:1, 24 h, r.t.; conc. aq. NH3/dioxane 1:1, 15 h, 55°C.
  • Robles , J. , Pedroso , E. and Grandas , A. 1994 . Int. J. Peptide Protein Res. , 43 : 359 – 362 . Protected peptide Ac-Ser(Ac)-Gly-Asp(OFm)-NH2 was obtained by acetylation of the side chain hydroxyl group of the serine residue of peptide Ac-Ser-Gly-Asp(OFm)-NH2. For the preparation of Ac-Ser-Gly-Asp(OFm)-NH2
  • Montserrat , F. X. , Grandas , A. , Eritja , R. and Pedroso , E. 1994 . Tetrahedron , 50 : 617 – 2622 .
  • Robles , J. , Pedroso , E. and Grandas , A. 1994 . Tetrahedron Lett. , 35 : 4449 – 4452 .
  • Vu , H. , McCollum , C. , Jacobson , K. , Theisen , P. , Vinayak , R. , Spiess , E. and Andrus , A. 1990 . Tetrahedron Lett. , 31 : 7269 – 7272 .

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