Synthesis of Glycosphingolipids (GSLs)

Abstract

Glycosphingolipids are a diverse family of biologically important glycolipids. They are directly involved in various molecular recognition events. Besides variations on the lipid component, more than 300 naturally occurring glycosphingolipid glycans have been identified. However, only a limited number of glycosphingolipids has been synthesized so far. Most of these compounds are produced by chemical synthetic approaches. Several enzymatic and chemoenzymatic approaches have been recently developed for the synthesis of these important glycoconjugates. Most recently, highly efficient one-pot multienzyme (OPME) systems have been combined with facile C18-cartridge-based purification schemes for high-yield and cost-effective production of glycosphingolipids. Glycosphingolipid structures that have been synthesized and the different strategies applied are summarized here. Future efforts are needed to expand the repertoire of synthetic glycosphingolipids, not only to provide standards and probes for research, but also to facilitate the development of potential glycosphingolipid-based diagnostics and therapeutics.

Chemoenzymatic Synthesis and Facile Purification of Gangliosides

“…Currently, the most common approach to obtaining gangliosides is by isolation from animal brain, but the type of structures that can be accessed by this method is limited, and high purity is difficult to achieve due to variations in the glycan and lipid components. Among synthetic strategies for obtaining gangliosides, glycosyltransferase‐based chemoenzymatic methods are attractive (Abhishek Santra, Yu, & Chen, 2019). They allow high‐yield synthesis of products with the desired glycosyl linkage with precise regio‐ and stereo‐controls without the need for tedious protection and deprotection procedures required by chemical synthesis.…”