Synthesis of a Glycolipid Analogue Towards the Design of a Biomimetic Cell Membrane

The Atrium, University of Guelph Institutional Repository

Synthesis of a Glycolipid Analogue Towards the Design of a Biomimetic Cell Membrane

Show simple item record

dc.contributor.advisor Auzanneau, France-Isabelle
dc.contributor.author Singh, Serena
dc.date 2012-07-26
dc.date.accessioned 2012-08-17T15:09:34Z
dc.date.available 2012-08-17T15:09:34Z
dc.date.issued 2012-08-17
dc.identifier.uri http://hdl.handle.net/10214/3855
dc.description.abstract 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. en_US
dc.description.sponsorship Natural Sciences and Engineering Research Council of Canada (NSERC) en_US
dc.language.iso en en_US
dc.subject 6-Thio pseudo glycolipid analogues en_US
dc.subject Carbohydrate-based tether en_US
dc.subject Bilayer lipid membrane en_US
dc.title Synthesis of a Glycolipid Analogue Towards the Design of a Biomimetic Cell Membrane en_US
dc.type Thesis en_US
dc.degree.programme Chemistry en_US
dc.degree.name Master of Science en_US
dc.degree.department Department of Chemistry en_US


Files in this item

Files Size Format View
Serena Singh MSc Thesis.pdf 2.317Mb PDF View/Open

This item appears in the following Collection(s)

Show simple item record

Search the Atrium


Advanced Search

Browse

My Account