Institute of Industrial Science, University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan.
Chem Biodivers. 2010 Feb;7(2):440-6. doi: 10.1002/cbdv.200900176.
A glycolipid analogue, GM4-type ganglioside, was obtained by a combination of chemical synthesis and biosynthetic processes in animal cells with dodecyl beta-D-galactoside (Gal C12) as primer. The primer was conveniently prepared in two steps: glycosylation, followed by deacetylation. The primer was introduced to mouse melanoma B16 cells to serve as substrate for cellular, enzyme-catalyzed glycosylation. Incubation of the cells in the presence of the primer resulted in sialylation of the galactose residue to afford a GM4 analogue that was released from the cells to the culture medium. The strategy of preparation of the GM4 analogue described in this study is a viable alternative to the existing methods. The saccharide-primer method is fast, convenient, not requiring expensive enzymes and glycosyl donors, and highly stereoselective.
一种糖脂类似物 GM4 型神经节苷脂通过化学合成和动物细胞生物合成过程的结合获得，以十二烷基 β-D-半乳糖苷（Gal C12）为引物。引物通过两步方便地制备：糖苷化，然后脱乙酰化。将引物引入小鼠黑色素瘤 B16 细胞作为细胞酶催化糖基化的底物。在存在引物的情况下孵育细胞导致半乳糖残基的唾液酸化，从而得到从细胞释放到培养基中的 GM4 类似物。本研究中描述的 GM4 类似物的制备策略是现有方法的可行替代方案。糖基化-引物法快速、方便，不需要昂贵的酶和糖基供体，具有高度的立体选择性。
