title: First synthesis of fully modified 4'-selenoRNA and 2'-OMe-4'-selenoRNA based on the mechanistic considerations of an unexpected strand break.
abstract: This study investigated oligonucleotide (ON) synthesis containing 4'-selenoribonucleoside(s) under standard phosphoramidite conditions. Careful operation using a manual ON synthetic system revealed that an unexpected strand break occurred to afford a C2-symmetric homodimer as a byproduct. In addition, this side reaction occurred during I2 oxidation. On the basis of these findings, the first synthesis of fully modified 4'-selenoRNA and 2'-OMe-4'-selenoRNA was achieved using tert-butyl hydroperoxide (TBHP) as the alternative oxidant.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokushima , Shomachi 1-78-1, Tokushima 770-8505, Japan.
authors.forename: Noriko
authors.initials: N
authors.lastname: Tarashima
authors.forename: Koya
authors.initials: K
authors.lastname: Hayashi
authors.forename: Maki
authors.initials: M
authors.lastname: Terasaki
authors.forename: Hirotsugu
authors.initials: H
authors.lastname: Taniike
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Inagaki
authors.forename: Kenji
authors.initials: K
authors.lastname: Hirose
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Furukawa
authors.forename: Akira
authors.initials: A
authors.lastname: Matsuda
authors.forename: Noriaki
authors.initials: N
authors.lastname: Minakawa
mesh_terms: D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D012313:RNA / Q000737:chemistry*; D012643:Selenium / Q000737:chemistry*; D020122:tert-Butylhydroperoxide / Q000737:chemistry*
chemical_list: D009841:Oligonucleotides; D009942:Organometallic Compounds; D016877:Oxidants; D012313:RNA; D020122:tert-Butylhydroperoxide; D012643:Selenium