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Attempts to prepare tethered bilayer lipid membranes using synthetic thioglycolipid anchors: synthesis of 6”-thiotrisaccharide glycolipid analogues and applications.

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dc.contributor.author Singh, Serena
dc.contributor.author Su, Zhangfei
dc.contributor.author Grossutti, Michael
dc.contributor.author Auzanneau, France-Isabelle
dc.date.accessioned 2015-12-01T18:39:41Z
dc.date.available 2016-03-14T05:00:14Z
dc.date.issued 2014-03-14
dc.identifier.issn 0008-6215
dc.identifier.uri http://hdl.handle.net/10214/9351
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. Glycosylation at position O-4’ of a propargyl cellobioside glycosyl acceptor and position O-6’ 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-β-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 µF/cm2 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. en_US
dc.description.sponsorship Natural Sciences and Engineering Research Council of Canada en_US
dc.language.iso en en_US
dc.publisher Elsevier en_US
dc.subject Bilayer Lipid Membrane en_US
dc.subject Carbohydrate Chemistry en_US
dc.subject Tethers en_US
dc.title Attempts to prepare tethered bilayer lipid membranes using synthetic thioglycolipid anchors: synthesis of 6”-thiotrisaccharide glycolipid analogues and applications. en_US
dc.type Article en_US
dc.degree.department Department of Chemistry en_US
dc.rights.license All items in the Atrium are protected by copyright with all rights reserved unless otherwise indicated.
dcterms.relation Carbohydr. Res. 390 (2014) 50–58


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