Hatanaka Kenichi
Institute of Industrial Science, The University of Tokyo, Tokyo, Japan.
Top Curr Chem. 2012;308:291-306. doi: 10.1007/128_2011_276.
A series of fluorous-tagged glycosides with different number of fluorine atoms are incorporated into the cells, transported to Golgi, elongated by cellular enzymes, and then released to the culture medium. Fluorine content strongly affects on the affinity for cell membrane and glycosylation. Essentially, the fluorocarbon chain in fluorous compound and the hydrocarbon chain are not miscible. However, the fluorous-tagged glycosides have affinity for cell membrane because of its amphiphilicity. The affinity of fluoro-amphiphilic compound for cell membrane is discussed using critical micelle concentration. The separation of glycosylated products by solvent extraction or fluorous solid phase extraction cartridges is also discussed.
一系列带有不同氟原子数目的氟代糖苷被导入细胞，转运至高尔基体，经细胞内酶延长，然后释放到培养基中。氟含量对细胞膜亲和力和糖基化有强烈影响。本质上，氟代化合物中的碳氟链与烃链是互不相溶的。然而，由于其两亲性，氟代糖苷对细胞膜具有亲和力。利用临界胶束浓度讨论了氟代两亲化合物对细胞膜的亲和力。还讨论了通过溶剂萃取或氟代固相萃取柱分离糖基化产物的方法。
