The synthesis of the three 6”-deoxy-6”-thio glycolipid analogues β-D-Gal-(1→6)-β-D-Gal-(1→4)-β-D-Glu-(1→OCH2)-[1,2,3]-triazole-1-dodecane, β-D-Gal-(1→4)-β-D-Glu-(1→4)- β-D-Glu-(1→OCH2)-[1,2,3]-triazole-1-dodecane and β-D-Gal-(1→4)-β-D-Glu-(1→4)-β-D-Glu-(1→OCH2)-[1,2,3]-triazole-1-octadecane is presented here. Glycosylation at position O-4’ of a propargyl cellobioside glycosyl acceptor and position O-6’ of a propargyl lactoside glycosyl acceptor with a 6-thio-6-deoxy 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) was assessed primarily by differential capacitance experiments. Deposition of a bilayer of DMPC/cholesterol (70:30) by Langmuir-Blodgett (LB) transfer followed by Langmuir-Schaefer (LS) touch to a self-assembled monolayer of the O-6’ linked analogue, diluted with 1-β-D-thioglucose, failed. This led to simplifying the target architecture to diagnose the quality of the monolayers. A monolayer of the known monosaccharide 1-octadecane-4-(6-thio-β-D-galacto-pyranosyloxymethyl)-[1,2,3]-triazole1 prepared by LB transfer was found to support a lipid monolayer deposited by LS touch and this bilayer had the lowest minimum capacitance observed of 0.9 µF/cm2. An attempt to produce a bilayer by the same method using the trisaccharide bearing the C-18 alkane chain failed and this was attributed to high water solubility, which gave rise to poor organization at the air-water interface. A self-assembled monolayer of this variant went forward to produce a poor quality bilayer with a minimum capacitance of 7.1 µF/cm2, which was the lowest value obtained for the trisaccharide series of analogues. / Natural Sciences and Engineering Research Council of Canada (NSERC)
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:OGU.10214/3855 |
| Date | 17 August 2012 |
| Creators | Singh, Serena |
| Contributors | Auzanneau, France-Isabelle |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Thesis |
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