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Conceptual "heat-driven" approach to the synthesis of DNA oligonucleotides on microarrays

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

  2. Author Address

    Beaucage, SL, US FDA, Ctr Biol Evaluat & Res, Div Therapeut Prot, 8800 Rockville Pike, Bethesda, MD 20892 USAUS FDA, Ctr Biol Evaluat & Res, Div Therapeut Prot, Bethesda, MD 20892 USA. NCI, Biol Testing Branch, Dev Therapeut Program, Frederick, MD 21701 USA. US Pharmacopeia, Rockville, MD 20852 USA.
    1. Year: 2003
  2. Book Title: THERAPEUTIC OLIGONUCLEOTIDES
  3. Series Title: ANNALS OF THE NEW YORK ACADEMY OF SCIENCES
    1. 1002
    2. Pages: 1-11
  5. Type of Work: Book Chapter
  1. Abstract:

    The discovery of deoxyribonucleoside cyclic N-acylphosphoramidites, a novel class of phosphoramidite monomers for solid-phase oligonucleotide synthesis, has led to the development of a number of phosphate protecting groups that can be cleaved from DNA oligonucleotides under thermolytic neutral conditions. These include the 2-(N-formyl-N-methyl) amino ethyl, 4-oxopentyl, 3-(N-tert-butyl)carboxamido-1-propyl, 3-(2-pyridyl)-1-propyl, 2-[N-methyl-N-(2-pyridyl)]aminoethyl, and 4-methythiobutyl groups. When used for 5'-hydroxyl protection of nucleosides, the analogous 1-phenyl-2-[N-methyl-N-(2-pyridyl)]aminoethyloxycarbonyI group exhibited excellent thermolytic properties, which may permit an iterative "heat-driven" synthesis of DNA oligonucleotides on microarrays. In this regard, progress has been made toward the use of deoxyribonucleoside cyclic N-acylphosphoramidites in solid-phase oligonucleotide syntheses without nucleobase protection. Given that deoxyribonucleoside cyclic N-acylphosphoramidites produce oligonucleotides with heat-sensitive phosphate protecting groups, blocking the 5'-hydroxyl of these monomers with, for example, the thermolabile 1-phenyl-2-[N-methyl-N-(2pyridyl)]aminoethyloxycarbonyl group may provide a convenient thermocontrolled method for the synthesis of oligonucleotides on microarrays

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