Synthesis and Characterization of Maltose-Based Amphiphiles as Supramolecular Hydrogelators

Abstract

Low molecular mass amphiphilic glycolipids have been prepared by linking a maltose polar head and a hydrophobic linear chain either by amidation or copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. The liquid crystalline properties of these amphiphilic materials have been characterized. The influence of the chemical structure of these glycolipids on the gelation properties in water has also been studied. Glycolipids obtained by the click coupling of the two components give rise to stable hydrogels at room temperature. The fibrillar structure of supramolecular hydrogels obtained by the self-assembly of these gelators have been characterized by electron microscopy. Fibers showed some torsion, which could be related with a chiral supramolecular arrangement of amphiphiles, as confirmed by circular dichroism (CD). The sol-gel transition temperature was also determined by differential scanning calorimetry (DSC) and NMR.

Supramolecular Hydrogels Based on Glycoamphiphiles: Effect of the Disaccharide Polar Head

“…Lactose octaacetate 25 (1) and N-propargyl palmitoylamide (4) 18 were synthesized according to a previously described procedure.…”

Synthesis, surface properties, and biocompatibility of 1,2,3-triazole-containing alkyl β-d-xylopyranoside surfactants

“…Triazole-linked glucose-based surfactants have been synthesized previously either by the copper-catalyzed azide alkyne cycloaddition (CuAAC) reaction of a glycosyl azide and a propargylated fatty alcohol or a propargylated sugar and an alkyl azide. 14-17 In this paper we report the synthesis and characterization of physiochemical properties of xylose-based carbohydrates containing a triazole linker as well as a preliminary biocompatibility assessment.…”

New insights into the transitional behaviour of methyl-6-O-(n-dodecanoyl)-α-D-glucopyranoside using variable temperature FTIR spectroscopy and X-ray diffraction

“…[8][9][10] Their exciting application potential includes their use as hydrogels or electrolytes whose physical properties can be tuned by external stimuli such as UV light or mechanical forces. [11][12][13][14][15] It is clear that the successful design of new liquid crystal carbohydrates now requires an improved understanding of the empirical relationships between molecular structure and aggregation behaviour. With that aim, recently, we studied the transitional behaviour of a series of monosaccharides, the methyl-6-O-(n-acyl)-α-D-glucopyranosides, as a function of the alkyl chain length, n. [16] At sufficiently high values of n, the compounds exhibit thermotropic liquid crystallinity, specifically, a monotropic smectic A phase seen on cooling from the isotropic phase, and which can be supercooled by ca 30ºC prior to crystallising.…”