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Synthesis of a 4-Thio Pseudo-Glycolipid to be used as a Tether for the Improvement of Lipid Bilayer Models

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Title: Synthesis of a 4-Thio Pseudo-Glycolipid to be used as a Tether for the Improvement of Lipid Bilayer Models
Author: Priske, Gillian
Department: Department of Chemistry
Program: Chemistry
Advisor: Auzanneau, France-Isabelle
Abstract: The cell membrane is a complex structure with many functions that can affect cellular processes. For this reason, a model possessing characteristics similar to those of the natural cell membrane is required for the investigation of various functions and properties belonging to this important structure. Presented is the synthesis of a glycolipid analogue possessing both a C-4’ thiol functionalization (for binding to an Au(111) electrode) and an anomeric triazole-linked phytanyl chain (for integration into a phospholipid bilayer). Additionally, a similar analogue without thiol functionalization was synthesized for use as a dilution molecule to prevent aggregation of the tether analogue during monolayer assembly. Aqueous compartments will exist above and below the bilayer allowing for future integration and functional analysis of membrane proteins. Glycosylation at the anomeric position of a lactosyl donor with propargyl alcohol gave a propargyl lactoside that underwent several steps of selective protection to give access at O-4’ for triflation. Displacement of the triflate gave a thioacetate functionalized disaccharide. Both the propargyl lactoside and the thioacetate functionalized disaccharide underwent copper-catalyzed azide-alkyne cycloadditions with phytanyl azide. Subsequent deprotections gave two novel glycolipid analogues.
URI: http://hdl.handle.net/10214/7727
Date: 2013-12


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