Chemoenzymatic syntheses of tumor-associated carbohydrate antigen Globo-H and stage-specific embryonic antigen 4
Chemoenzymatic syntheses of tumor-associated carbohydrate antigen Globo-H and stage-specific embryonic antigen 4
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DOI：
10.1002/adsc.200800129
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发表时间：
2008-08-01
影响因子：
5.4
通讯作者：
Huang, Xuefei
中科院分区：
文献类型：
--
作者：
Wang, Zhen;Gilbert, Michel;Huang, Xuefei
神经节苷脂由于当时重要的生物学特性而备受关注。在此，我们报告了两种 Globo 系列神经节苷脂寡糖 Globo-H I 和阶段特异性胚胎抗原 4 (SSEA-4) 2 的首次化学酶合成。使用基于预激活的一锅糖基化方法快速组装了这两种化合物的共同前体 SSEA-3 五糖。 SSEA-3 中形成 1,2-顺式键的立体选择性归因于供体的空间支撑效应，而不是糖基供体的电子特性。然后，SSEA-3 成功地被岩藻糖基转移酶 WbsJ 岩藻糖基化，并被唾液酸转移酶 CST-I 和 PmST1 唾液酸化，分别产生 Globo-H 和 SSEA-4。
Gangliosides have attracted much attention due to then important biological properties. Herein we report the first chemoenzymatic syntheses of two globo series of ganglioside oligosaccharides, Globo-H I and stage-specific embryonic antigen-4 (SSEA-4) 2. The common precursor SSEA-3 pentasaccharide for these two compounds was assembled rapidly using the pre-activation-based one-pot glycosylation method. The stereoselectivity in forming the 1,2-cis linkage in SSEA-3 was attributed to a steric buttressing effect of the donor rather than electronic properties of the glycosyl donors. SSEA-3 was then successfully fucosylated by the fucosyltransferase WbsJ and sialylated by sialyltransferases CST-I and PmST1 producing Globo-H and SSEA-4, respectively.