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Facile preparation of DNA-tagged carbohydrates.

Bioorganic & medicinal chemistry letters (2003-07-23)
Shinsuke Sando, Kazuki Matsui, Yusuke Niinomi, Nobuhiko Sato, Yasuhiro Aoyama
PMID12873482
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.

MATERIALS
Product Number
Brand
Product Description
296945
Sigma-Aldrich
Sodium cyanoborohydride solution, 5.0 M in 1 M NaOH
296813
Sigma-Aldrich
Sodium cyanoborohydride solution, 1.0 M in THF
156159
Sigma-Aldrich
Sodium cyanoborohydride, reagent grade, 95%