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The 2-(N-formyl-N-methyl)aminoethyl group as a potential phosphate/thiophosphate protecting group in solid-phase oligodeoxyribonucleotide synthesis

  1. Author:
    Grajkowski, A.
    Wilk, A.
    Chmielewski, M. K.
    Phillips, L. R.
    Beaucage, S. L.

  2. Author Address

    US FDA, Ctr Biol Evaluat & Res, Div Therapeut Prot, 8800 Rockville Pike, Bethesda, MD 20892 USA. US FDA, Ctr Biol Evaluat & Res, Div Therapeut Prot, Bethesda, MD 20892 USA. NCI, Biol Tresting Branch, Dev Therapeut Program, Frederick, MD 21701 USA. Beaucage SL US FDA, Ctr Biol Evaluat & Res, Div Therapeut Prot, 8800 Rockville Pike, Bethesda, MD 20892 USA.
    1. Year: 2001
  2. Journal: Organic Letters
    1. 3
    2. 9
    3. Pages: 1287-1290
  4. Type of Article: Article
  1. Abstract:

    [GRAPHICS] The 2-(N-formyl-N-methyl)aminoethyl deoxyribonucleoside phosphoramidite 1 has been synthesized and used in the solid-phase synthesis of an octadecathymidylic acid as a cost-efficient monomer for potential application in the preparation of therapeutic oligonucleotides, The 2-(N-formyl-N- methyl)aminoethyl group can be cleaved from oligonucleotides according to a unique thermolytic cyclodeesterification process at pH 7.0. In addition to being cost-effective, the use of 1 simplifies oligonucleotide postsynthesis processing by eliminating the utilization of concentrated ammonium hydroxide in oligonucleotide deprotection.

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