Fluorous-tagged compound: A viable scaffold to prime oligosaccharide synthesis by cellular enzymes

Maria Carmelita Z. Kasuya, Reuben Cusi, Orie Ishihara, Atsushi Miyagawa, Kazuhiko Hashimoto, Toshinori Sato, Kenichi Hatanaka

研究成果: Article査読

25 被引用数 (Scopus)

抄録

Fluorous-tagged saccharide primers could be viable scaffolds for the synthesis of oligosaccharides. This research demonstrates that a fluorine-containing saccharide derivative could actually be taken up by the cell, the saccharide chain elongated by cellular enzymes, and the elongated product released by the cells to the culture medium. A fluorous-tagged lactoside primer, 6-(perfluorohexyl)hexyl-4-O-(β-D-galactopyranosyl)- β-D-glucopyranoside, was chemically synthesized and introduced in mouse B16 cells to prime oligosaccharide synthesis. Uptake of the primer by B16 cells resulted in the sialylation of the terminal galactose residue to afford an oligosaccharide with the same glycan structure as ganglioside GM3. The presence of many fluorine atoms did not have any adverse effects to the cells. Moreover, the number of fluorine atoms did not pose a steric barrier and instead, their presence possibly increased the hydrophobicity of the primer and enhanced membrane permeability. This strategy of using a fluorous-tagged primer and cells can pave the way for an easier way of preparing oligosaccharides via an environment-friendly approach that eliminates the use of large amounts of organic solvents.

本文言語English
ページ(範囲)599-604
ページ数6
ジャーナルBiochemical and Biophysical Research Communications
316
3
DOI
出版ステータスPublished - 2004 4 9

ASJC Scopus subject areas

  • 生物理学
  • 生化学
  • 分子生物学
  • 細胞生物学

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