Solid-phase synthesis of stereoregulated oligodeoxyribonucleoside phosphorothioates

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Solid-phase synthesis of stereoregulated oligodeoxyribonucleoside phosphorothioates
2006
Natsuhisa Oka, Mika Yamamoto, Terutoshi Sato and Takeshi Wada
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8562, Japan
Nucleic Acids Symposium Series 2006
An efficient stereocontrolled synthesis of oligodeoxyribonucleoside phosphorothioates on a solid-support by an oxazaphospholidine method was achieved. A detailed investigation on the reagents and conditions for the solid-phase synthesis revealed that the use of the capping and sulfurizing reagents which are regularly used for the conventional synthesis of phosphorothioate DNA resulted in a sluggish removal of the chiral auxiliaries on the phosphorothioate internucleotidic linkages. After optimization of the capping and sulfurizing steps, the deprotection of the internucleotidic linkages were successfully conducted under the regular basic conditions, and P-stereoregulated phosphorothioate DNA oligomers were successfully obtained with excellent diastereopurity.
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