title: The aggregation behaviour of two structurally isomeric glycolipids.
abstract: The two structurally isomeric glycolipids N-octyl-(1-hexadecylamido)-beta-D-glucopyranoside (Glc-N-[8/16]) and N-hexadecyl-(1-octylamido)-beta-D-glucopyranoside (Glc-N[16/8]) were synthesized. The lyotropic phase behaviour of these isomers was investigated in order to determine the extent to which the relative disposition of the alkyl chains with respect to the amide unit affects the aggregation properties of the amphiphiles. Both isomers exhibit lamellar and inverse topology cubic mesophases. The extent and polymorphism of the non-lamellar phases appear to be more pronounced in the Glc-N-[8/16] isomer relative to the Glc-N-[16/8] isomer. A molecular mechanics study was undertaken in an attempt to rationalize this behaviour.
authors: Department of Chemistry, University of Southampton, UK.
authors: G S
authors: GS
authors: Attard
authors: W P
authors: WP
authors: Blackaby
authors: A R
authors: AR
authors: Leach
mesh_terms: D002240:Carbohydrate Sequence; D006017:Glycolipids / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008969:Molecular Sequence Data; D013696:Temperature
chemical_list: D006017:Glycolipids