| RRC ID |
39883
|
| 著者 |
Kasuya MC, Wang LX, Lee YC, Mitsuki M, Nakajima H, Miura Y, Sato T, Hatanaka K, Yamagata S, Yamagata T.
|
| タイトル |
Azido glycoside primer: a versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues.
|
| ジャーナル |
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.
|
| 巻・号 |
329(4)
|
| ページ |
755-63
|
| 公開日 |
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
|
| 引用数 |
41
|
|
WOS 分野
|
CHEMISTRY, ORGANIC
CHEMISTRY, APPLIED
BIOCHEMISTRY & MOLECULAR BIOLOGY
|
| リソース情報 |
| ヒト・動物細胞 |
B16 |
