Biomaterial Database

Stereocontrolled synthesis of phosphorothioate DNA by an oxazaphospholidine approach. 2003

Takeshi Wada, and Natsuhisa Oka, and Kazuhiko Saigo

Department of Integrated Biosciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Bldg 702, Kashiwa, Chiba 277-8562, Japan.

Stereocontrolled synthesis of oligodeoxyribonucleoside phosphorothioates using nucleoside 3'-O-oxazaphospholidine derivatives as monomer units is described. N-(Cyanomethyl)pyrrolidinium triflate (CMPT) was found to be effective as an activator for the highly diastereoselective internucleotidec bond formation. The present method was applied to the solid-phase synthesis of stereoregulated oligodeoxyribonucleoside phosphorothioates.

UI	MeSH Term	Description	Entries
D009943	Organophosphorus Compounds	Organic compounds that contain phosphorus as an integral part of the molecule. Included under this heading is broad array of synthetic compounds that are used as PESTICIDES and DRUGS.	Organophosphorus Compound,Organopyrophosphorus Compound,Organopyrophosphorus Compounds,Compound, Organophosphorus,Compound, Organopyrophosphorus,Compounds, Organophosphorus,Compounds, Organopyrophosphorus
D002851	Chromatography, High Pressure Liquid	Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed.	Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D004247	DNA	A deoxyribonucleotide polymer that is the primary genetic material of all cells. Eukaryotic and prokaryotic organisms normally contain DNA in a double-stranded state, yet several important biological processes transiently involve single-stranded regions. DNA, which consists of a polysugar-phosphate backbone possessing projections of purines (adenine and guanine) and pyrimidines (thymine and cytosine), forms a double helix that is held together by hydrogen bonds between these purines and pyrimidines (adenine to thymine and guanine to cytosine).	DNA, Double-Stranded,Deoxyribonucleic Acid,ds-DNA,DNA, Double Stranded,Double-Stranded DNA,ds DNA
D013873	Thionucleotides	Nucleotides in which the base moiety is substituted with one or more sulfur atoms.