Preparation of oligodeoxyribonucleoside alkyl or arylphosphonate

Details Preparation of oligodeoxyribonucleoside alkyl or arylphosphonate Preparation of oligodeoxyribonucleoside alkyl or arylphosphonate

1983-10-07

1985-03-26

Foelak, Morton

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

536 27, 536 28, 536 29, C07H 2102, C07H 2104

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045074330

ABSTRACT:
Process for synthesizing deoxyribonucleoside methylphosphonates on polystyrene polymer supports which involves condensing 5'-dimethoxytrityldeoxynucleoside 3'-methylphosphonates. The oligomers are removed from the support and the base protecting groups hydrolyzed by treatment with ethylenediamene in ethanol, which avoids hydrolysis of the methylphosphonate linkages. Two types of oligomers are synthesized: those containing only methylphosphonate linkages, d-Np(Np).sub.n N, and those which terminate with a 5' nucleotide residue, dNp(Np).sub.n N. The latter oligomers can be phosphorylated by polynucleotide kinase, and are separated by polyacrylamide gel electrophoresis according to their chain length. Piperidine randomly cleaves the oligomer methylphosphonate linkages and generates a series of shorter oligomers whose number corresponds to the length of the original oligomer. Apurinic sites introduced by acid treatment spontaneously hydrolyze to give oligomers which terminate with free 3' and 5'-OH groups. These reactions may be used to characterize the oligomers.

REFERENCES:
patent: 4056673 (1977-11-01), Heimer et al.
Matteucci et al., "Synthesis of Deoxyoligonucleotides on a Polymer Support", J. Am. Chem. Soc., 1981, v. 103, pp. 3185-3191.

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