Reference - Detail
| 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 Fluorocarbons 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 | 2.985 |
| Times Cited | 25 |
| WOS Category | BIOPHYSICS BIOCHEMISTRY & MOLECULAR BIOLOGY |
| Altmetric score |
オルトメトリクス指標項目
|
| The most frequently cited source | Patent(IFI CLAIMS) |
| Total number of mentions | 1 |
| Altmetric score changes over past 6months | 0.0 |
| Resource | |
| Human and Animal Cells | B16 cells |