Solid-supported diphosphitylating and triphosphitylating reagents for nucleoside modification.
Curr Protoc Nucleic Acid Chem
; Chapter 13: Unit 13.8, 2008 Jun.
Article
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| MEDLINE
| ID: mdl-18551427
ABSTRACT
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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Compostos Organofosforados
/
Nucleosídeos
Idioma:
En
Revista:
Curr Protoc Nucleic Acid Chem
Ano de publicação:
2008
Tipo de documento:
Article
País de afiliação:
Estados Unidos