Stereocontrolled synthesis of LNA dinucleoside phosphorothioate by the oxathiaphospholane approach.
The application of the oxathiaphospholane approach for the stereocontrolled synthesis of LNA dinucleoside phosphorothioate is described. The reaction of ring opening condensation proceeds in CH3CN solution in high yield and with over 96% stereoselectivity. One of diastereomers of LNA dinucleoside phosphorothioate (presumably R(P)) was found to be readily digested by svPDE.
Karwowski
B
B
Department of Bioorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Lódź.
Okruszek
A
A
Wengel
J
J
Stec
W J
WJ
D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D009690:Nucleic Acid Conformation; D009711:Nucleotides / Q000138:chemical synthesis* / Q000378:metabolism; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000378:metabolism*; D010710:Phosphates / Q000138:chemical synthesis*; D043264:Phosphodiesterase I; D010727:Phosphoric Diester Hydrolases / Q000378:metabolism*; D012266:Ribose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism; D013237:Stereoisomerism
C434798:2'-O-4'-C-methylene-ribofuranosyl nucleotide; D009711:Nucleotides; D009841:Oligonucleotides; D010710:Phosphates; C434797:oxathiaphospholane; D012266:Ribose; C083120:phosphorodithioic acid; D010727:Phosphoric Diester Hydrolases; D043264:Phosphodiesterase I