RRC ID 42115
Author Kasuya MC, Cusi R, Ishihara O, Miyagawa A, Hashimoto K, Sato T, Hatanaka K.
Title Fluorous-tagged compound: a viable scaffold to prime oligosaccharide synthesis by cellular enzymes.
Journal Biochem Biophys Res Commun
Abstract 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-(beta-D-galactopyranosyl)-beta-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.
Volume 316(3)
Pages 599-604
Published 2004-4-9
DOI 10.1016/j.bbrc.2004.02.094
PII S0006291X0400364X
PMID 15033442
MeSH Animals Biochemistry / methods* Carbohydrate Sequence Chromatography, High Pressure Liquid Culture Media / chemistry Culture Media / pharmacology Fluorine / chemistry* Fluorine / pharmacokinetics G(M3) Ganglioside / chemistry Glycosides / chemistry Glycosylation Lactose / analogs & derivatives Lactose / chemistry* Magnetic Resonance Spectroscopy Melanoma, Experimental Mice Models, Chemical Molecular Sequence Data Oligosaccharides / biosynthesis Oligosaccharides / chemical synthesis* Solvents / chemistry Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Time Factors
IF 2.705
Times Cited 25
Human and Animal Cells