The synthesis of neoglycophospholipid conjugates via reductive amination of omega-oxoalkylglycosides and phosphatidylethanolamines.
Phospholipid conjugates of mono- and disaccharides tethered with an n-decanyl spacer were efficiently synthesized via an improved reductive amination of deprotected omega-oxodecanyl beta-glycosides and phosphatidylethanolamines with or without alkenyl groups. The omega-oxodecanyl beta-glycosides were prepared by stereoselective glycosidation of glycosyl halides with 1, 10-decanediol followed by pyridinium dichromate oxidation. The acetyl groups of the omega-oxodecanyl beta-glycosides were removed with sodium methoxide prior to their conjugation with phosphatidylethanolamines.
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Emory University School of Medicine, Department of Surgery, Atlanta, GA 30322, USA.
Chaikof
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D002240:Carbohydrate Sequence; D006027:Glycosides; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D010714:Phosphatidylethanolamines; D010743:Phospholipids / Q000138:chemical synthesis*
D006027:Glycosides; D007202:Indicators and Reagents; D010714:Phosphatidylethanolamines; D010743:Phospholipids