Kurimoto Kenta, Yamamura Hatsuo, Miyagawa Atsushi
Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan.
Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan.
Carbohydr Res. 2015 Jan 12;401:39-50. doi: 10.1016/j.carres.2014.10.018. Epub 2014 Oct 29.
Cell-surface glycans containing sialic acid are involved in various biological phenomena. However, the syntheses of GM4 derivatives with (2 → 2) and (2 → 4) linkages have not been investigated to date. In this study, sialylation of all of the hydroxyl groups on galactose were investigated for the syntheses of GM4 isomers. Regioselective sialylation was achieved via protection of galactosyl acceptors using electron-rich benzyl groups. These synthetic sialylated glycans will prove to be useful tools for studying unidentified carbohydrate-mediated biological roles.
含有唾液酸的细胞表面聚糖参与多种生物学现象。然而，迄今为止尚未对具有(2→2)和(2→4)连接的GM4衍生物的合成进行研究。在本研究中，为了合成GM4异构体，对半乳糖上所有羟基的唾液酸化反应进行了研究。通过使用富电子苄基对半乳糖基受体进行保护实现了区域选择性唾液酸化。这些合成的唾液酸化聚糖将被证明是研究未知的碳水化合物介导的生物学作用的有用工具。
