Solid-supported diphosphitylating and triphosphitylating reagents for nucleoside modification.
This unit describes procedures for synthesis of diphosphitylating and triphosphitylating reagents. The synthesized reagents are first immobilized on appropriate polymer-bound linkers. Rigid and sterically hindered polymer-bound diphosphitylating and triphosphitylating reagents are then reacted selectively with the 5'-hydroxyl group of nucleosides in the presence of excess nucleosides. Typical oxidation with tert-butyl hydroperoxide, deprotection, and final cleavage of the products from the resins using a trifluoroacetic acid cocktail afford various nucleoside 5'-O-diphosphate and nucleoside 5'-O-triphosphate analogs. The use of the diphosphitylating and polymer-bound diphosphitylating reagents in preparation of oligodeoxynucleotides containing diphosphodiester internucleotide bridges is also described. This solid-phase strategy allows for the synthesis of the phosphorylated compounds without the need for nucleoside phosphate precursors, protected nucleosides, or purification of intermediates.
University of Rhode Island, Kingston, Rhode Island, USA.
Yousef
Y
Ahmadibeni
Keykavous
K
Parang
D000438:Alcohols / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009711:Nucleotides / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry
D000438:Alcohols; D004952:Esters; D007202:Indicators and Reagents; D009705:Nucleosides; D009711:Nucleotides; D009943:Organophosphorus Compounds; D011108:Polymers