Practical and Reliable Synthesis of 1,2-Dideoxy-d-ribofuranose and its Application in RNAi Studies

Nucleosides, Nucleotides & Nucleic Acids
Yuki NagayaYukio Kitade

Abstract

We developed a practical and reliable method for synthesizing an abasic deoxyribonucleoside, 1,2-dideoxy-d-ribofuranose (dR(H)) via elimination of nucleobase from thymidine. To synthesize oligonucleotides bearing dR(H) by the standard phosphoramidite solid-phase method, dR(H) was converted to the corresponding phosphoramidite derivative and linked to a solid support (controlled pore glass resin). Chemically modified small interfering RNAs (siRNAs) possessing dR(H) at their 3'-overhang regions were synthesized. Introducing dR(H) to the 3'-end of the antisense strand of siRNA reduced its knockdown effect.

References

Dec 11, 1993·Nucleic Acids Research·J B ThomsonF Eckstein
May 30, 2002·Biochemistry·Yu Lin JiangJames T Stivers
May 10, 2003·The Journal of Organic Chemistry·Jeong-Seok Han, Todd L Lowary
Sep 12, 2008·Bioorganic & Medicinal Chemistry Letters·Yoshihito UenoYukio Kitade
Feb 10, 2009·Bioorganic & Medicinal Chemistry·Yoshihito UenoYukio Kitade
Jul 13, 2011·Organic & Biomolecular Chemistry·Saúl Martínez-MonteroMiguel Ferrero
Aug 22, 2012·Angewandte Chemie·Mitsuru NaitoKazunori Kataoka
Apr 18, 2013·Journal of the American Chemical Society·Vijay SinghEric T Kool
Jun 8, 2013·Bioorganic & Medicinal Chemistry Letters·Xiong LuoYukio Kitade
Apr 24, 2014·Angewandte Chemie·Lik Hang YuenEric T Kool

❮ Previous
Next ❯

Citations

Nov 3, 2016·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Yoshiaki Kitamura
Aug 4, 2018·Science·Kyle W KnousePhil S Baran

❮ Previous
Next ❯

Methods Mentioned

BETA
electrophoresis
column chromatography
column
NMR
transfection

Related Concepts

Related Feeds

Carbapenems

Carbapenems are members of the beta lactam class of antibiotics and are used for the treatment of severe or high-risk bacterial infections. Discover the latest research on carbapenems here.

Carbapenems (ASM)

Carbapenems are members of the beta lactam class of antibiotics and are used for the treatment of severe or high-risk bacterial infections. Discover the latest research on carbapenems here.