Facile synthesis of stable lipid analogues possessing a range of alkyl groups: application to artificial glycolipids

Abstract

Efficient preparation of lipid analogues is described in which various long alkoxy chains and 2-hydroxyethyl group were covalently linked with benzoic acid derivatives. An alpha-mannopyranosyl group was stereoselectively introduced by the conventional imidate method into the terminal hydroxy group without any alternation of other moieties in a molecule. The resulting new glycoconjugates acted as models of natural glycolipids for protein-carbohydrate interactions.