The synthesis of neoglycophospholipid conjugates via reductive amination of omega-oxoalkylglycosides and phosphatidylethanolamines

Carbohydr Res. 1998 Feb;307(1-2):77-81. doi: 10.1016/s0008-6215(98)00032-9.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carbohydrate Sequence
  • Glycosides*
  • Indicators and Reagents
  • Molecular Sequence Data
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxidation-Reduction
  • Phosphatidylethanolamines*
  • Phospholipids / chemical synthesis*

Substances

  • Glycosides
  • Indicators and Reagents
  • Phosphatidylethanolamines
  • Phospholipids