Abstract
Triaryloxydichlorophosphoranes were tested as condensing agents for oligodeoxyribonucleotide synthesis in the phosphotriester method. Tris(2,4,6-tribromophenoxy)dichlorophosphorane (BDCP) was found to be a relatively stable crystalline material which could be used as a chemical reagent. A notable feature of the BDCP-promoted condensation reaction was studied by 31P-NMR. A small amount of BDCP compared to the conventional condensing agent was effective for the generation of active nucleotide intermediates and BDCP itself was quantitatively converted into an inert material, tris(2,4,6-tribromophenyl)phosphate (2). Thus, BDCP enabled us to separate the activation step from the condensation process in the phosphotriester method. This preactivation method was applied to the solid-phase synthesis.
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- Efimov V. A., Chakhmakhcheva O. G., Ovchinnikov YuA Improved rapid phosphotriester synthesis of oligodeoxyribonucleotides using oxygen-nucleophilic catalysts. Nucleic Acids Res. 1985 May 24;13(10):3651–3666. doi: 10.1093/nar/13.10.3651. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Efimov V. A., Reverdatto S. V., Chakhmakhcheva O. G. New effective method for the synthesis of oligonucleotides via phosphotriester intermediates. Nucleic Acids Res. 1982 Nov 11;10(21):6675–6694. doi: 10.1093/nar/10.21.6675. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Letsinger R. L., Lunsford W. B. Synthesis of thymidine oligonucleotides by phosphite triester intermediates. J Am Chem Soc. 1976 Jun 9;98(12):3655–3661. doi: 10.1021/ja00428a045. [DOI] [PubMed] [Google Scholar]
- Seth A. K., Jay E. A study of the efficiency and the problem of sulfonation of several condensing reagents and their mechanisms for the chemical synthesis of deoxyoligoribonucleotides. Nucleic Acids Res. 1980 Nov 25;8(22):5445–5459. doi: 10.1093/nar/8.22.5445. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Zarytova V. F., Knorre D. G. General scheme of the phosphotriester condensation in the oligodeoxyribonucleotide synthesis with arylsulfonyl chlorides and arylsulfonyl azolides. Nucleic Acids Res. 1984 Feb 24;12(4):2091–2110. doi: 10.1093/nar/12.4.2091. [DOI] [PMC free article] [PubMed] [Google Scholar]