Synthesis of 6-thio pseudo glycolipids and their orientation on a gold slide studied by IRRAS.
We have synthesized four 6-thio pseudo glycolipid analogues and assessed how two of them self-assembled on a gold surface. These structures were designed as candidate tethers molecules to anchor bilayer lipid membranes on gold. 6-Deoxy-6-thiogalactose was chosen to anchor the macromolecule to the gold and define an aqueous zone at the gold surface. A long alkane chain (C-12 or C-18) linked to the anomeric position of the sugar residue was chosen to anchor a bilayer lipid membrane. The linkage between the carbohydrate and the hydrophobic chains is either a glycosidic bond or a 1,4-disubstituted triazole formed by copper(I)-catalysed alkyne-azide cycloaddition (CuAAC) of the propargyl glycoside with azido-dodecane and azido-octadecane. We are expecting that the hydrocarbon chains will orient themselves perpendicular to the gold surface and be incorporated into the first leaflet of the bilayer membrane. We have studied self assembled monolayers of the C-12 aglycone analogues on gold using infrared reflection absorption spectroscopy (IRRAS). We compared the results given by the IRRAS experiments to the IR spectra recorded by attenuated total reflection (ATR) spectroscopy on films of the randomly oriented analogues. Our results demonstrate that the C-12 analogues did bind to gold and did orient themselves perpendicular to the gold slide.
Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.
Mickael
M
Guillemineau
Serena
S
Singh
Michael
M
Grossutti
France-Isabelle
FI
Auzanneau
D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D008051:Lipid Bilayers / Q000737:chemistry; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared
D006017:Glycolipids; D008051:Lipid Bilayers