title: Synthesis and biological properties of chemically modified siRNAs bearing 1-deoxy-D-ribofuranose in their 3'-overhang region.
abstract: To elucidate the role of the sugar moiety in the two natural nucleotides of the 3'-overhang region of small interfering RNA (siRNA), we synthesized siRNAs that incorporated two abasic nucleosides, 1-deoxy-D-ribofuranose (R(H)). We improved the method for preparing an O-protected abasic nucleoside, 1-deoxy-2,3,5-tri-O-benzoyl-β-D-ribofuranose, via the reductive cleavage of the anomeric position of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose. To incorporate R(H) into oligonucleotides by the standard phosphoramidite solid phase method, R(H) was converted into its phosphoramidite derivative and the solid support linked to a controlled pore glass resin. Chemically modified RNAs possessing R(H) at the 3'-overhang region were easily prepared in good yields. siRNAs containing R(H) showed moderate nuclease-resistance and a desirable knockdown effect.
authors.affiliation: Department of Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
authors.forename: Kazumi
authors.initials: K
authors.lastname: Taniho
authors.forename: Remi
authors.initials: R
authors.lastname: Nakashima
authors.forename: Mahmoud
authors.initials: M
authors.lastname: Kandeel
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Kitamura
authors.forename: Yukio
authors.initials: Y
authors.lastname: Kitade
mesh_terms: D003855:Deoxyribose / Q000031:analogs & derivatives* / Q000737:chemistry*; D020868:Gene Silencing; D017930:Genes, Reporter; D005822:Genetic Vectors; D006367:HeLa Cells; D006801:Humans; D049410:Luciferases, Renilla / Q000235:genetics; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D020871:RNA Stability; D034741:RNA, Small Interfering / Q000138:chemical synthesis* / Q000235:genetics; D014162:Transfection
chemical_list: D009705:Nucleosides; D009943:Organophosphorus Compounds; D034741:RNA, Small Interfering; C434331:phosphoramidite; D003855:Deoxyribose; D049410:Luciferases, Renilla