Halmos T, Santarromana M, Antonakis K, Scherman D
UMR 133 CNRS/Rhône-Poulenc Rorer, Laboratoire de Chimie Organique Biologique, Villejuif, France.
Carbohydr Res. 1997 Mar 26;299(1-2):15-21. doi: 10.1016/s0008-6215(96)00328-x.
In order to obtain hydrophilic analogues of 1,4-dimethylsulfonyloxybutane (busulfan) with enhanced selectivity and improved brain penetration, we have synthesized 6-O-methylsulfonyl-D-glucose, 3-O-methylsulfonyl-D-glucose, 3,6-di-O-methylsulfonyl-D-glucose, 4-O-methylsulfonyl-D-glucose, and 4,6-di-O-methylsulfonyl-D-glucose, and we have studied their interactions with the human erythrocyte GLUT1 hexose transport system. Mesylation of OH-4 and OH-6 of glucose resulted in a slightly diminished affinity for the GLUT1 glucose transporter, whereas mesylation of OH-3 led to complete loss of affinity.
为了获得具有更高选择性和更好脑渗透性的1,4 - 二甲磺酰氧基丁烷（白消安）的亲水性类似物，我们合成了6 - O - 甲基磺酰基 - D - 葡萄糖、3 - O - 甲基磺酰基 - D - 葡萄糖、3,6 - 二 - O - 甲基磺酰基 - D - 葡萄糖、4 - O - 甲基磺酰基 - D - 葡萄糖和4,6 - 二 - O - 甲基磺酰基 - D - 葡萄糖，并研究了它们与人红细胞GLUT1己糖转运系统的相互作用。葡萄糖的OH - 4和OH - 6甲磺酰化导致对GLUT1葡萄糖转运蛋白的亲和力略有降低，而OH - 3甲磺酰化导致亲和力完全丧失。
