Lehmann J, Scheuring M
Institut für Organische Chemie und Biochemie der Universität Freiburg, Germany.
Carbohydr Res. 1995 Oct 16;276(1):57-74. doi: 10.1016/0008-6215(95)00145-j.
Starting from pentaerythritol, photolabile mono-, di-, and tri-dentate galactose derivatives as well as their 3H-labelled isotopomers were synthesised. The hydrophilic chains linking the 6 position of D-galactose to pentaerythritol consist of 13 atoms in line. The mono-, di- and tri-dentate compounds, although themselves not transported, inhibit in increasing order 14C-D-galactose transport into erythrocytes. On irradiating whole cells in the presence of ligand with 350-nm UV light, these compounds also in increasing order, could irreversibly block the hexose transport system. Irradiation without ligand has no effect. By using the 3H-labelled tridentate galactose compound the hexose transporter (zone 4.5) is specifically radiolabelled, as could be shown in an SDS-PAGE of membrane proteins from erythrocytes previously photoaffinity labelled. Radiolabelling is significantly suppressed in the presence of D-glucose.
从季戊四醇出发，合成了光不稳定的单齿、双齿和三齿半乳糖衍生物及其3H标记的同位素异构体。将D-半乳糖6位与季戊四醇相连的亲水链由13个原子直线排列组成。单齿、双齿和三齿化合物自身虽不被转运，但能以递增顺序抑制14C-D-半乳糖向红细胞内的转运。在配体存在下用350 nm紫外光照射全细胞时，这些化合物也能以递增顺序不可逆地阻断己糖转运系统。无配体照射则无作用。通过使用3H标记的三齿半乳糖化合物，己糖转运体（4.5区）被特异性放射性标记，这在先前经光亲和标记的红细胞膜蛋白的SDS-PAGE中得到了证实。在D-葡萄糖存在下，放射性标记显著受到抑制。
