Facile preparation of DNA-tagged carbohydrates.
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.
Sando
Shinsuke
S
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan.
Matsui
Kazuki
K
Niinomi
Yusuke
Y
Sato
Nobuhiko
N
Aoyama
Yasuhiro
Y
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
D001894:Borohydrides; D002241:Carbohydrates; D005936:Glucans; D009841:Oligonucleotides; C031146:maltoheptaose; D004247:DNA; C009282:sodium cyanoborohydride