Alberta Glycomics Centre, Department of Chemistry , University of Alberta , Edmonton , Alberta T6G 2G2 , Canada.
Chem Rev. 2018 Sep 12;118(17):8188-8241. doi: 10.1021/acs.chemrev.8b00070. Epub 2018 Jul 6.
The plasma membrane of cells contains a diverse array of lipids that provide important structural and biological features. Glycolipids are typically a minor component of the cell membrane and consist primarily of glycosphingolipids (GSLs). GSLs in vertebrates contain a multifarious assortment of glycan headgroups, which can be important to biological functions based on lipid-lipid and lipid-protein interactions. The design of probes to study these complex targets requires advanced synthetic methodologies. In this Review, we will discuss recent advances in chemical and chemoenzymatic synthesis of GSLs in conjunction with the use of these approaches to design new probes. Examples using either chemical or enzymatic semisynthesis methods starting from isolated GSLs will also be reviewed. Focusing primarily on vertebrate glycolipids, we will highlight examples of radionuclide, fluorophore, photoresponsive, and bioorthogonal tagged GSL probes.
细胞膜含有多种脂质，为细胞提供了重要的结构和生物学特征。糖脂通常是细胞膜的次要成分，主要由糖鞘脂（GSLs）组成。脊椎动物中的 GSL 含有多种多样的聚糖头基，这些头基基于脂质-脂质和脂质-蛋白相互作用，对生物功能很重要。设计用于研究这些复杂靶标的探针需要先进的合成方法。在这篇综述中，我们将讨论 GSL 的化学和化学酶法合成的最新进展，并结合这些方法来设计新的探针。我们还将回顾使用从分离的 GSL 开始的化学或酶半合成方法的实例。主要关注脊椎动物糖脂，我们将重点介绍放射性核素、荧光团、光响应和生物正交标记的 GSL 探针的实例。
