Chemical Synthesis of Phosphatidylglucoside

• DOI: 10.1007/978-1-0716-2910-9_6
• Publication Date: 2023-01-01T04:01:09Z
• Authors: Koki Kano; Nozomi Ishii; Peter Greimel; Ichiro Matsuo
• Keywords: Aqueous medium

1-stearoyl (18:0)-2-arachidoyl (20:0)-sn-glycero-3-phospho-ß-D-glucoside (Phosphatidylglucoside or PtdGlc) was synthesized by direct coupling of D-glucose with the phosphate group of phosphatidic acid (18:0, 20:0). Selective in situ activation of the anomeric center of D-glucose by 2-chloro-1,3-dimethylimidazolinium chloride (DMC) in aqueous media allows the omission of protecting groups while furnishing the required ß-phosphate linkage with high selectivity. The described method is suitable to access PtdGlc in mg scale utilizing a simple two step purification protocol.