Application of a solid-phase beta-triphosphitylating reagent in the synthesis of nucleoside beta-triphosphates.
A beta-triphosphitylating reagent was subjected to reaction with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound beta-triphosphitylating reagent. The solid-phase reagent was reacted with unprotected nucleosides (e.g., 3'-azido-3'-deoxythymidine, cytidine, thymidine, uridine, inosine, or adenosine) in the presence of 1H-tetrazole. Polymer-bound nucleosides underwent oxidation with t-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford only monosubstituted 5'-O-beta-triphosphorylated nucleosides.
Ahmadibeni
Yousef
Y
Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, Rhode Island 02881, USA.
Parang
Keykavous
K
D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010756:Phosphoric Acids / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry; D011137:Polystyrenes / Q000737:chemistry*
D000577:Amides; D009705:Nucleosides; D009711:Nucleotides; D009943:Organophosphorus Compounds; D010756:Phosphoric Acids; D011108:Polymers; D011137:Polystyrenes; C011067:phosphoramidic acid