title: N-linked glycolipids by Staudinger coupling of glycosylated alkyl diazides with fatty acids.
abstract: Aiming for new glycolipids with enhanced chemical stability and close structural similarity to natural cell membrane lipids for the development of a drug delivery system, we have synthesized double amide analogs of glyco-glycerolipids. The synthesis applied a Staudinger reaction based coupling of a 1,3-diazide with fatty acid chlorides. While the concept furnished the desired glucosides in reasonable yields, the corresponding lactosides formed a tetrahydropyrimidine based 1:1 coupling product instead. This unexpected coupling result likely originates from steric hindrance at the iminophosphorane intermediate and provides an interesting core structure for potentially bioactive surfactants. The assembly behavior of both glycolipid types was investigated by optical polarizing microscopy, DSC and surface tension studies.
authors.affiliation: Chemistry Department, Faculty of Science, University of Malaya, Lembah Pantai, 50603 Kuala Lumpur, Malaysia.
authors.forename: Salih Mahdi
authors.initials: SM
authors.lastname: Salman
authors.forename: Thorsten
authors.initials: T
authors.lastname: Heidelberg
authors.forename: Hairul Anuar
authors.initials: HA
authors.lastname: Bin Tajuddin
mesh_terms: D001386:Azides / Q000737:chemistry*; D005227:Fatty Acids / Q000737:chemistry*; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D001386:Azides; D005227:Fatty Acids; D006017:Glycolipids