New phosphoramidates as protecting groups in ribooligonucleotides synthesis.
N, N-Dimethyl-p-phenylenediamine, glycine amide and p-methylthioaniline were condensed with uridine 5'-phosphate and the phosphoramidates obtained were tested for their stability in anhydrous pyridine, 50% aqueous pyridine or 80% acetic acid. The p-methylthioanilidate (IIc) was oxidized to give p-methylsulfoxylanilidate of uridine 5'-phosphate (IId) which was found to be 5 times more stable than the p-methylthio compound. The p-methylsulfoxylanilidate of 2'-O-benzoyluridine 3'-phosphate was condensed with the mononucleotide to yield the dinucleotide, MMTrU(OBz)-p-U(OBz)-p in 28% yield.
D000577:Amides; D002854:Chromatography, Paper; D008722:Methods; D009841:Oligonucleotides / Q000138:chemical synthesis*; D009843:Oligoribonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds; D010655:Phenylenediamines; D010756:Phosphoric Acids; D013056:Spectrophotometry, Ultraviolet
D000577:Amides; D009841:Oligonucleotides; D009843:Oligoribonucleotides; D009943:Organophosphorus Compounds; D010655:Phenylenediamines; D010756:Phosphoric Acids; C011067:phosphoramidic acid