Synthesis and aggregation behaviour of symmetric glycosylated bolaamphiphiles in water

Abstract

This work is dedicated to the Professor Armand Lattes for his great contribution to the organic and supramolecular chemistry AbstractThe 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

Ordered liquids and hydrogels from alkenyl succinic ester terminated bola-amphiphiles for large-scale applications

“…Besides hydrophobicity stemming from dimer fatty acids in the polymer backbone we have investigated the effect of hydrophobic aliphatic side groups in the aand b-position to the ionic head group on the self-assembly. The role of double-stranded bolaform architecture has already been addressed in the context of vesicle formation of symmetrical glycosylated bola-amphiphiles 11 making reference to similar asymmetric molecules where hydrophobic chains were attached at the anomeric site of the head groups' furanose ring. 12 In the present study the head groups result from nucleophilic addition of an a,u-polyesterdiol (PES) on alkenyl succinic anhydrides (ASA) which have been proposed for numerous technical applications and are used on a large scale, e.g.…”

Synthesis, chemistry, physicochemical properties and industrial applications of amino acid surfactants: A review

“…The unusual β-amino acids used may be sugar amino acid, an AZT-derived amino acid, a norbornene amino acid, and an AZTderived amino alcohol (Scheme 4). Polidori et al, 2006 has also given synthesis of symmetric bolaamphiphiles derived from tris (hydroxymethyl) aminomethane (Tris) (Scheme 4).…”