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Synthesis of phosphorodithioate DNA by the H-phosphonothioate method

✍ Scribed by Peter H. Seeberger; Marvin H. Caruthers; Danute Bankaitis-Davis; Graham Beaton

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
863 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

A novel method for the efficientsynthesis phosphorodithioate DNA using H-phosphonothioate synthons is described. The 5'-DMT-nucleoside H-phosphonothioate monomers were prepared in two high yielding steps from commercially available phosphoramidites. This strategy for the synthesis of Hphosphonothioate monomers proved versatile and allowed for the synthesis of cholesterol Hphosphonothioate synthons. Synthetic protocols for the assembly of phosphorodithioate DNA using an automated synthesizer were developed. The H-phosphonothioate solid-phase synthesis method facilitates the preparation of oligonucleotide conjugates, as demonstrated by the example of attachment of 5'cholesterol oligonucleotidas.

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Simple and efficient synthesis of a new H-phosphonothionylating reagent, 9fluorenemethyl H-phosphonothioate, was developed. The synthetic utility of the reagent has been demonstrated in the preparations of nucleoside H-phosphonothioate, nucleoside phosphorothioate, and nucleoside phosphorodithioate