肿瘤相关碳水化合物抗原Globo-H和阶段特异性胚胎抗原4的化学酶法合成
Chemoenzymatic Syntheses of Tumor-Associated Carbohydrate Antigen Globo-H and Stage-Specific Embryonic Antigen 4.
作者信息
Wang Zhen, Gilbert Michel, Eguchi Hironobu, Yu Hai, Cheng Jiansong, Muthana Saddam, Zhou Luyuan, Wang Peng George, Chen Xi, Huang Xuefei
机构信息
Department of Chemistry, The University of Toledo, 2801 W. Bancroft Street, MS 602, Toledo, Ohio 43606 USA.
出版信息
Adv Synth Catal. 2008 Aug 4;350(11-12):1717-1728. doi: 10.1002/adsc.200800129.
Abstract
Gangliosides have attracted much attention due to their important biological properties. Herein, we report the first chemoenzymatic syntheses of two globo series of ganglioside oligosaccharides, Globo-H 1 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.
摘要
神经节苷脂因其重要的生物学特性而备受关注。在此，我们报道了两种球系列神经节苷脂寡糖Globo-H 1和阶段特异性胚胎抗原-4（SSEA-4）2的首次化学酶促合成。使用基于预活化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1,2-顺式连接形成的立体选择性归因于供体的空间支撑效应而非糖基供体的电子性质。然后，SSEA-3通过岩藻糖基转移酶WbsJ成功进行岩藻糖基化，并通过唾液酸转移酶CST-I和PmST1进行唾液酸化，分别产生Globo-H和SSEA-4。
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