Reference - Detail
| RRC ID | 39883 |
|---|---|
| Author | Kasuya MC, Wang LX, Lee YC, Mitsuki M, Nakajima H, Miura Y, Sato T, Hatanaka K, Yamagata S, Yamagata T. |
| Title | Azido glycoside primer: a versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues. |
| Journal | Carbohydr Res |
| Abstract |
A lactoside primer, 12-azidododecyl beta-lactoside, was synthesized via the Koenigs-Knorr method by glycosylation of 1,12-dodecyldiol with perbenzoylated lactosyl bromide. The presence of the 2-O-acyl substituent in the donor gave the beta-lactoside, and an excess of acceptor ensured monoglycosylation of the diol. Mesylation of the omega-hydroxyl group in the aglycon, followed by displacement of the mesylate with azide and subsequent O-debenzoylation gave the desired omega-azidododecyl beta-lactoside. The azido glycoside primer was examined in mouse B16 melanoma cells for its feasibility as a building block for oligosaccharide biosynthesis. Uptake of the azido glycoside primer by B16 cells resulted in the sialylation of the galactose residue of the primer to give a glycosylated product having the same glycan as in ganglioside GM3. After 24 h incubation of B16 cells with the primers, the amount of sialylated omega-azidododecyl beta-lactoside primer was 75% of the amount of sialylated n-dodecyl beta-lactoside. However, after 48 h incubation, both primers gave equal amounts of the sialylated products. Interestingly, the remaining azido glycoside primer after 48 h incubation was 5.6-fold greater than that of the alkyl primer, indicating degradation of the alkyl primer to a larger extent than the omega-azido glycoside primer. The facile chemical synthesis and the efficient uptake in cells make the azido glycoside primer a versatile building block for the biocombinatorial synthesis of glycolipid oligosaccharides. |
| Volume | 329(4) |
| Pages | 755-63 |
| Published | 2000-12-1 |
| DOI | 10.1016/s0008-6215(00)00238-x |
| PII | S000862150000238X |
| PMID | 11125817 |
| MeSH | Animals Azides / chemical synthesis* Azides / chemistry* Azides / metabolism Azides / pharmacology Biological Transport Cell Division / drug effects G(M3) Ganglioside / analogs & derivatives G(M3) Ganglioside / chemistry Glycosides / chemical synthesis* Glycosides / chemistry Glycosides / metabolism* Glycosides / pharmacology Glycosphingolipids / biosynthesis* Glycosphingolipids / chemistry* Glycosylation Humans Lactose / analogs & derivatives Lactose / chemical synthesis* Lactose / chemistry* Lactose / metabolism Lactose / pharmacology Melanoma, Experimental Mice Molecular Structure Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Tumor Cells, Cultured |
| IF | 1.841 |
| Times Cited | 41 |
| WOS Category | CHEMISTRY, ORGANIC CHEMISTRY, APPLIED BIOCHEMISTRY & MOLECULAR BIOLOGY |
| Altmetric score |
オルトメトリクス指標項目
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| 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 |