Attempts to prepare tethered bilayer lipid membranes using synthetic thioglycolipid anchors: synthesis of 6 %26apos;%26apos;-thiotrisaccharide glycolipid analogues and applications

作者：Singh Serena; Su Zhangfei; Grossutti Michael; Auzanneau France Isabelle^*

来源：Carbohydrate Research, 2014, 390: 50-58.

DOI：10.1016/j.carres.2014.03.007

• Thiotrisaccharide glycolipids
• Click chemistry
• Artificial bilayer lipid membranes

The synthesis of the three 6 %26apos;%26apos;-deoxy-6 %26apos;%26apos;-thio glycolipid analogues beta-D-Gal-(1 -%26gt; 6)-beta-D-Gal-(1 -%26gt; 4)-beta-D-Glu(1 -%26gt; OCH2)-[1,2,3]-triazole-1-dodecane, beta-D-Gal-(1 -%26gt; 4)-beta-D-Glu-(1 -%26gt; 4)-beta-D-Glu-(1 -%26gt; OCH2)-[1,2,3]-triazole-1-dodecane and beta-D-Gal-(1 -%26gt; 4)-beta-D-Glu-(1 -%26gt; 4)-beta-D-Glu-(1 -%26gt; OCH2)-[1,2,3]-triazole-1-octadecane is presented. Glycosylation at position O-4%26apos; of a propargyl cellobioside glycosyl acceptor and position O-6%26apos; of a propargyl lactoside glycosyl acceptor with a 6-deoxy-6-thio galactosyl donor gave rise to two unique trisaccharides that in turn underwent copper-catalyzed azide-alkyne cycloadditions with either 1-azidododecane or 1-azidooctadecane. The potential for each of these analogues to function as tethers of lipid bilayers to Au( 111) surface was assessed by differential capacitance experiments. A monolayer of the previously described monosaccharide 1-octadecane-4-(6-thio-beta-D-galacto-pyranosyloxymethyl)[1,2,3]-triazole either self-assembled or prepared by Langmuir-Blodgett (LB) transfer was found to support an outer leaflet monolayer (DMPC/cholesterol, 70:30) deposited by Langmuir-Schaefer (LS) touch. The bilayers obtained with this monosaccharide analogue had minimum differential capacitances of 1.0 and 0.9 mu F/cm(2) when the inner monolayer was prepared by self-assembly and LS touch, respectively. Attempts to produce bilayers using the trisaccharides synthesized here were unsuccessful; we are attributing these unsuccessful results mostly to the high water solubility of trisaccharides combined with the relatively short length of the hydrocarbon chains used in this study.

• 出版日期2014-5-22