The synthesis of 16-mercaptohexadecanyl glycosides for biosensor applications.
The Pk trisaccharide and the central disaccharide element of asialo GM1 activated as their trichloroacetimidates were each used to glycosylate 16-(p-toluensulfonyloxy) hexadecanol 1. Displacement of the tosyl group by thiocyanate followed by sodium borohydride reduction and saponification afforded oligosaccharide 16-mercaptohexadecanyl glycosides that were isolated as the corresponding disulfides 6 and 17 unless oxygen was rigorously excluded from the solvents used for work-up. Dithiothreitol reduction of disulfides and subsequent isolation under an inert atmosphere with degassed solvents gave the thiols 7 and 18. Chemisorption of omega-glycosyl alkanethiols and alkanethiols onto gold electrodes produces self-assembled monolayers that can act as amperometric biosensors for the detection of proteins that bind to the immobilized oligosaccharide epitope.
Department of Chemistry, University of Alberta, Edmonton, Canada.
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Kitov
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Railton
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Bundle
D015374:Biosensing Techniques; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000737:chemistry; D005677:G(M1) Ganglioside / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008969:Molecular Sequence Data; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*; D014312:Trisaccharides / Q000737:chemistry
D004187:Disaccharides; D006027:Glycosides; D013438:Sulfhydryl Compounds; D014312:Trisaccharides; C033878:N-acetylgalactosaminyl-(1-4)-galactose; D005677:G(M1) Ganglioside; C113460:globotriose; C018835:asialo GM1 ganglioside