Highly efficient solid phase synthesis of oligonucleotide analogs containing phosphorodithioate linkages

A triester method for the synthesis of deoxynucleoside phosphorodithioate dimers is described. The phosphorodithioate linkage is introduced using a new dithiophosphorylating reagent DPSE-SP(S)Cl(2) where DPSE = 2-diphenylmethylsilylethyl. This group is removed quickly using tetra-butylammonium fluor...

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Detalhes bibliográficos
Main Authors: Capaldi, Daniel C., Cole, Douglas L., Ravikumar, Vasulinga T.
Formato: Artigo
Idioma:en
Publicado em: Oxford University Press 2000
Assuntos:
NAR Methods Online
Acesso em linha:https://ncbi.nlm.nih.gov/pmc/articles/PMC103313/
https://ncbi.nlm.nih.gov/pubmed/10756207
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Descrição
Resumo:A triester method for the synthesis of deoxynucleoside phosphorodithioate dimers is described. The phosphorodithioate linkage is introduced using a new dithiophosphorylating reagent DPSE-SP(S)Cl(2) where DPSE = 2-diphenylmethylsilylethyl. This group is removed quickly using tetra-butylammonium fluoride leading to the quantitative formation of phosphorodithioate diesters uncontaminated with the corresponding phosphorothioates. The utility of this group is demonstrated by the synthesis of a pentadecathymidylic acid, [T(PS(2))T(PO(2))](7)T, which contains alternating phosphorodithioate/phosphate diester internucleotide linkages.