title: Facile preparation of DNA-tagged carbohydrates.
abstract: We report here that unprotected carbohydrates (maltose, lactose, cellobiose, and maltoheptaose) can be attached to the aminoalkylated oligonucleotides under mild reductive-amination conditions (aqueous borate buffer, pH 8.0, NaBH(3)CN, 60 degrees C) without notable side reactions. Quadruplex-forming G-rich oligonucleotide, 5'-aminoalkyl d(TGGGGT), is glycosylated with maltoheptaose to afford a novel DNA-assisted tetrasaccharide cluster motif.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan.
authors.forename: Shinsuke
authors.initials: S
authors.lastname: Sando
authors.forename: Kazuki
authors.initials: K
authors.lastname: Matsui
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Niinomi
authors.forename: Nobuhiko
authors.initials: N
authors.lastname: Sato
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Aoyama
mesh_terms: D000478:Alkylation; D000586:Amination; D001894:Borohydrides / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D004247:DNA / Q000138:chemical synthesis / Q000737:chemistry*; D054856:G-Quadruplexes; D005936:Glucans / Q000737:chemistry; D006031:Glycosylation; D008956:Models, Chemical; D009841:Oligonucleotides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
chemical_list: D001894:Borohydrides; D002241:Carbohydrates; D005936:Glucans; D009841:Oligonucleotides; C031146:maltoheptaose; D004247:DNA; C009282:sodium cyanoborohydride