title: Practical and Reliable Synthesis of 1,2-Dideoxy-d-ribofuranose and its Application in RNAi Studies.
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.
authors.affiliation: a United Graduate School of Drug Discovery and Medical Information Sciences, Gifu University , 1-1 Yanagido, Gifu , Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Nagaya
authors.affiliation: b Department of Biomolecular Science , Graduate School of Engineering, Gifu University , 1-1 Yanagido, Gifu , Japan.|c Department of Chemistry and Biomolecular Science , Faculty of Engineering, Gifu University , 1-1 Yanagido, Gifu , Japan.
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Kitamura
authors.affiliation: b Department of Biomolecular Science , Graduate School of Engineering, Gifu University , 1-1 Yanagido, Gifu , Japan.
authors.forename: Remi
authors.initials: R
authors.lastname: Nakashima
authors.affiliation: b Department of Biomolecular Science , Graduate School of Engineering, Gifu University , 1-1 Yanagido, Gifu , Japan.|c Department of Chemistry and Biomolecular Science , Faculty of Engineering, Gifu University , 1-1 Yanagido, Gifu , Japan.
authors.forename: Aya
authors.initials: A
authors.lastname: Shibata
authors.affiliation: a United Graduate School of Drug Discovery and Medical Information Sciences, Gifu University , 1-1 Yanagido, Gifu , Japan.|b Department of Biomolecular Science , Graduate School of Engineering, Gifu University , 1-1 Yanagido, Gifu , Japan.|c Department of Chemistry and Biomolecular Science , Faculty of Engineering, Gifu University , 1-1 Yanagido, Gifu , Japan.
authors.forename: Masato
authors.initials: M
authors.lastname: Ikeda
authors.affiliation: a United Graduate School of Drug Discovery and Medical Information Sciences, Gifu University , 1-1 Yanagido, Gifu , Japan.|b Department of Biomolecular Science , Graduate School of Engineering, Gifu University , 1-1 Yanagido, Gifu , Japan.|c Department of Chemistry and Biomolecular Science , Faculty of Engineering, Gifu University , 1-1 Yanagido, Gifu , Japan.
authors.forename: Yukio
authors.initials: Y
authors.lastname: Kitade
mesh_terms: D003855:Deoxyribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015870:Gene Expression; D020868:Gene Silencing; D017930:Genes, Reporter; D006367:HeLa Cells; D006801:Humans; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D034622:RNA Interference; D034741:RNA, Small Interfering / Q000235:genetics*
chemical_list: D009841:Oligonucleotides; D034741:RNA, Small Interfering; D003855:Deoxyribose; C043138:1,2-dideoxyribofuranose
keywords: Abasic nucleoside; RNAi; glycal; oligonucleotide; siRNA