Kiso M, Furui H, Ando K, Ishida H, Hasegawa A
Department of Applied Bioorganic Chemistry, Gifu University, Japan.
Bioorg Med Chem. 1994 Nov;2(11):1295-308. doi: 10.1016/s0968-0896(00)82080-5.
A systematic synthesis of the N-methyl-1-deoxynojirimycin-containing oligosaccharides related to the Lewis x, Lewis a, sialyl-Lewis x and sialyl-Lewis a antigens has been achieved. The couplings of the suitably protected 1-deoxynojirimycin derivative 10 with methyl-1-thioglycosides (glycosyl donors) of L-fucose (11), D-galactose (15) and alpha-sialyl-(2-->3)-D-galactose (27) were carried out by using dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide/trifluoromethanesulfonic acid (NIS/TfOH) as the glycosyl promoter. The resulting di- and tri-saccharides were each converted, by further cross glycosylations with 11, 15 or 27, to the desired tri- and tetra-saccharides 3-6 that inhibit the recognition between sialyl-Lewis x and selectins, a family of leukocyte cell adhesion molecules.
已实现对与Lewis x、Lewis a、唾液酸化Lewis x和唾液酸化Lewis a抗原相关的含N-甲基-1-脱氧野尻霉素的寡糖进行系统合成。使用三氟甲磺酸二甲硫鎓盐（DMTST）或N-碘代琥珀酰亚胺/三氟甲磺酸（NIS/TfOH）作为糖基化促进剂，使适当保护的1-脱氧野尻霉素衍生物10与L-岩藻糖（11）、D-半乳糖（15）和α-唾液酰基-（2→3）-D-半乳糖（27）的甲基硫代糖苷（糖基供体）进行偶联反应。通过与11、15或27进一步进行交叉糖基化反应，将所得的二糖和三糖分别转化为所需的抑制唾液酸化Lewis x与选择素（一类白细胞细胞粘附分子）之间识别作用的三糖和四糖3-6。
