PMID: 3768335Sep 9, 1986Paper

Solid-phase syntheses of oligodeoxyribonucleoside methylphosphonates

Biochemistry
P S MillerC H Agris

Abstract

Oligodeoxyribonucleoside methylphosphonates of defined sequence of the type d-Np(NP)nN, where n is 6-13, are readily prepared on insoluble polystyrene supports by use of protected 5'-(dimethoxytrityl)deoxyribonucleoside 3'-(methylphosphonic imidazolides) as synthetic intermediates. The imidazolides are prepared in situ by reaction of protected 5'-(dimethoxytrityl)deoxyribonucleoside with methylphosphonic bis(imidazolide) and can be stores in the reaction solution for up to 2 weeks at 4 degrees C with no loss in activity. The condensation reaction is accelerated by the presence of tetrazole, which appears to act as an acid catalyst. The half-life for dimer formation on the polystyrene support is 5 min, and the reaction is 95% complete after 60 min. Although similar kinetics are observed when controlled pore glass is used as the support, the extent of the reaction does not go beyond 78%, even after prolonged incubation. In order to simplify purification and sequence analysis of the oligomer, the 5'-terminal nucleoside unit is linked via a phosphodiester bond. This linkage may be introduced by either an o-chlorophenyl phosphotriester method or a cyanoethyl phosphoramidite method. The latter procedure simplifies the deprotection st...Continue Reading

Citations

May 1, 1992·Trends in Biotechnology·S Agrawal
Mar 31, 2000·Pharmacology & Therapeutics·A A KrayevskyM V Jasko
Nov 1, 1987·Proceedings of the National Academy of Sciences of the United States of America·M MatsukuraS Broder
Dec 1, 1993·Journal of Biomolecular Structure & Dynamics·Y ChoD G Gorenstein
Jun 10, 1988·Nucleic Acids Research·B FroehlerM Matteucci
Jun 11, 1991·Nucleic Acids Research·L Kibler-HerzogW D Wilson
May 11, 1993·Nucleic Acids Research·R I HogrefeL J Arnold
Feb 25, 1994·Nucleic Acids Research·N N PolushinJ S Cohen
Feb 10, 2000·Nucleic Acids Research·A A ArzumanovA A Krayevsky
Jul 11, 2003·Nucleic Acids Research·David SheehanDouglas J Dellinger
Jan 1, 1990·Annals of the New York Academy of Sciences·G Zon
Apr 29, 2015·Advanced Drug Delivery Reviews·Eric Wickstrom
Oct 1, 2008·Bioorganic & Medicinal Chemistry·Tatiana V AbramovaVladimir N Silnikov
Aug 1, 1988·Analytical Biochemistry·C J Marcus-Sekura
May 14, 2005·Bioorganicheskaia khimiia·A V StreletskiĭS E Esipov
Jan 1, 1993·Antisense Research and Development·T ZhuS Stein

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