A Diversity-Oriented Strategy for Chemical Synthesis of Glycosphingolipids: Synthesis of Glycosphingolipid LcGg4 and Its Analogues and Derivatives,The Journal of Organic Chemistry

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A Diversity-Oriented Strategy for Chemical Synthesis of Glycosphingolipids: Synthesis of Glycosphingolipid LcGg4 and Its Analogues and Derivatives
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-01-04 , DOI: 10.1021/acs.joc.0c02490
Rajendra S. Rohokale ₁ , Qingjiang Li ₁ , Zhongwu Guo ₁

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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 and N-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.

中文翻译：

糖鞘脂化学合成的面向多样性的策略：糖鞘脂LcGg4及其类似物和衍生物的合成

为合成糖鞘脂（GSLs）开发了一种面向多样性的策略。通过使用包含GSL聚糖和脂质核心结构的简单乳糖苷作为通用原料，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法对脂质进行现场重塑，从而获得了不同的合成靶标，从而突出了该策略和N-酰化。该策略已通过合成乳酸神经节GSL LcGg4（其是未分化的恶性骨髓细胞的生物标志物）及其一系列带有不同糖链和独特功能或分子标记的类似物或衍生物的方法得到了验证。该合成策略应广泛适用，因此，通过在每个糖基化之后使用不同的糖基化供体和不同的脂质重塑底物，可用于快速获得各种GSL和相关衍生物。

更新日期：2021-01-16

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