title: A concise synthesis of glycolipids based on aspartic acid building blocks.
abstract: L-aspartic acid building blocks bearing galactosyl moieties were used to synthesise glycolipid mimetics of variable hydrocarbon chain length. The glycolipids were readily prepared through amide bond formation using the TBTU/HOBt coupling methodology. It was observed that, under these conditions, activation of the α-carboxylic acid of the intermediates led to near complete racemisation of the chiral centre if the reaction was carried out in the presence of a base such as triethylamine. The enantiomerically pure glycolipids were obtained after careful consideration of the synthetic sequence and by performing the coupling reactions in the absence of base.
authors.affiliation: Department of Chemistry, National University of Ireland Maynooth, Co. Kildare, Ireland. trinidad.velascotorrijos@nuim.ie
authors.forename: Trinidad
authors.initials: T
authors.lastname: Velasco-Torrijos
authors.forename: Lorna
authors.initials: L
authors.lastname: Abbey
authors.forename: Roisin
authors.initials: R
authors.lastname: O'Flaherty
mesh_terms: D001224:Aspartic Acid / Q000737:chemistry*; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006017:Glycolipids; D001224:Aspartic Acid