Hada Noriyasu, Sonoda Yoshiko, Takeda Tadahiro
Kyoritsu University of Pharmacy, 1-5-30 Shibakoen, Tokyo 105-8512, Japan.
Carbohydr Res. 2006 Jul 24;341(10):1341-52. doi: 10.1016/j.carres.2006.04.019. Epub 2006 May 15.
A novel glycosphingolipid, beta-D-Manp-(1-->4)-[alpha-L-Fucp-(1-->3)]-beta-D-Glcp-(1-->1)-Cer, found in the millipede, Parafontaria laminata armigera, and multivalent derivatives of its carbohydrate moiety were synthesized. As the key step, the target glycolipid (1) was obtained through an inversion reaction at the 2-position of a beta-glucopyranoside residue yielding a beta-mannopyranoside. In addition, the synthesis of fluorescently labeled trimer and tetramer glycoconjugates (2, 3) was achieved by iterative amide bond formation using a monomer unit (24).
在千足虫Parafontaria laminata armigera中发现了一种新型糖鞘脂，β-D-甘露糖基-(1→4)-[α-L-岩藻糖基-(1→3)]-β-D-葡萄糖基-(1→1)-神经酰胺，并合成了其碳水化合物部分的多价衍生物。作为关键步骤，通过β-葡萄糖吡喃糖苷残基2位的构型翻转反应得到β-甘露糖吡喃糖苷，从而获得目标糖脂(1)。此外，使用单体单元(24)通过迭代酰胺键形成实现了荧光标记的三聚体和四聚体糖缀合物(2,3)的合成。
