One-pot selective deuteriation of 5′-dimethoxytritylated deoxynucleotide derivatives.

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Abstract

Procedures have been developed for selective incorporation of deuterium at C-6 of 5′-DMT-dC(Bz)@, C-8 of 5′-DMT-dA(Bz), C-8 of 5′-DMT-dG(i-Bu), and C-6 of 5′-DMT-dT in dimethylsulfoxide solution catalyzed by various amounts of base at 90–135°C with quantitative or nearly quantitative deuterium-labeling yields. The reactions of deuterium exchange of C-6 of 5′-DMT-dC(Bz), C-8 of 5′-DMT-dA(Bz), and C-8 of 5′-DMT-dG(i-Bu) were performed in a one-pot reaction procedure and that of C-6 of 5′-DMT-dT was achieved by deuteriation of 5′-unprotected dT, followed by dimethoxytritylation of 5′-OH with 4,4′-dimethoxytrityl chloride.

References (29)

  • J.W. Cheng et al.

    J. Mol. Biol.

    (1992)
  • S.H. Chou et al.

    J. Mol Biol.

    (1992)
  • R. Boelens et al.

    J. Mol. Struc.

    (1988)
  • U. Schmitz et al.

    J. Mol. Biol.

    (1991)
  • Y. Wang et al.

    J. Mol. Biol.

    (1991)
  • R. Macaya et al.

    J. Mol. Biol

    (1992)
  • J. Luo et al.

    FEBS

    (1992)
  • O. Kennard et al.

    Quart Rev. Biophys.

    (1989)
  • R.E. Dickerson et al.

    J. Biomol Struct. Dyn

    (1987)
  • A.D. DiGabriele et al.

    Proc. Natal. Acad. Sci. U.S.A.

    (1989)
  • A.H.-J. Wang et al.

    Science

    (1981)
  • M. McCall et al.

    Nature

    (1986)
  • F. Aboul-ela et al.

    Nucleic Acids Res.

    (1988)
  • G.R. Clark et al.

    Nucleic Acids Res.

    (1990)
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