Synthesis and aggregation behaviour of symmetric glycosylated bolaamphiphiles in water

Abstract

The synthesis of a new family of symmetric bolaamphiphiles derived from tris(hydroxymethyl)aminomethane (Tris) is described. The specific glycosylation of Tris hydroxyl groups allows modulation of their polar head volumes. Symmetric bolaamphiphiles were prepared by grafting the Tris moieties onto a hydrophobic chain through urea or amide bonds and a glycyl linker. Moreover, the introduction of phenyl groups or a perfluoroalkyl chain afforded increased rigidity of the hydrophobic spacer arm. A diluted water suspension of these amphiphiles did not show a supramolecular organisation any larger than micellar-type aggregates © ARKAT.