Chemical Synthesis of Phosphatidylglucoside

Koki Kano; Nozomi Ishii; Peter Greimel; Ichiro Matsuo

doi:10.1007/978-1-0716-2910-9_6

Chemical Synthesis of Phosphatidylglucoside

Methods Mol Biol. 2023:2613:73-78. doi: 10.1007/978-1-0716-2910-9_6.

Authors

Koki Kano¹, Nozomi Ishii¹, Peter Greimel², Ichiro Matsuo³

Affiliations

¹ Division of Molecular Science, Faculty of Science and Technology, Gunma University, Gunma, Japan.
² RIKEN Center for Brain Science, Saitama, Japan.
³ Division of Molecular Science, Faculty of Science and Technology, Gunma University, Gunma, Japan. matsuo@gunma-u.ac.jp.

PMID: 36587071
DOI: 10.1007/978-1-0716-2910-9_6

Abstract

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.

Keywords: 2-chloro-1,3-dimethylimidazolinium chloride; Chemical synthesis; D-glucose; Phosphatidylglucoside; bioactive lipid; ß-glycosylphosphate.

MeSH terms

Glucose*
Glucosides
Glycerophospholipids*

Substances

phosphatidylglucose
Glycerophospholipids
Glucose
Glucosides