A Diversity-Oriented Strategy for Chemical Synthesis of Glycosphingolipids: Synthesis of Glycosphingolipid LcGg4 and Its Analogues and Derivatives
A Diversity-Oriented Strategy for Chemical Synthesis of Glycosphingolipids: Synthesis of Glycosphingolipid LcGg4 and Its Analogues and Derivatives
复制标题
面向多样性的鞘糖脂化学合成策略：鞘糖脂LcGg4及其类似物和衍生物的合成
DOI：
10.1021/acs.joc.0c02490
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Guo, Zhongwu
中科院分区：
文献类型：
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作者：
Rohokale, Rajendra S.;Li, Qingjiang;Guo, Zhongwu
开发了一种以多样性为导向的鞘糖脂（GSL）合成策略。该策略的重点是使用含有 GSL 聚糖和脂质核心结构的简单乳糖苷作为通用起始材料，通过化学糖基化逐步延长聚糖并通过化学选择性交叉复分解和 N-酰化对脂质进行现场重塑，从而获得不同的合成目标。该策略通过乳神经节 GSL、LcGg4 的合成得到验证，LcGg4 是未分化恶性骨髓细胞的生物标志物，以及一系列携带不同糖链和独特功能或分子标签的类似物或衍生物。这种合成策略应该广泛适用，因此，通过使用不同的糖基化供体和每次糖基化后脂质重塑的不同底物，可用于快速获得各种 GSL 和相关衍生物。
A diversity-oriented strategy was developed for the synthesis of glycosphingolipids (GSLs). This strategy was highlighted by using a simple lactoside containing the core structures of GSL glycan and lipid as the universal starting material to obtain different synthetic targets upon stepwise elongation of the glycan via chemical glycosylations and on-site remodeling of the lipid via chemoselective cross-metathesis andN-acylation. The strategy was verified with the synthesis of a lacto-ganglio GSL, LcGg4, which is a biomarker of undifferentiated malignant myeloid cells, and a series of its analogues or derivatives carrying different sugar chains and unique functionalities or molecular labels. This synthetic strategy should be widely applicable and, therefore, be utilized to rapidly access various GSLs and related derivatives by using different donors for glycosylations and different substrates for lipid remodeling following each glycosylation.