THE SYNTHESIS OF 16-MERCAPTOHEXADECANYL GLYCOSIDES FOR BIOSENSOR APPLICATIONS

The P-k trisaccharide and the central disaccharide element of asialo G M(1) activated as their trichloroacetimidates were each used to glycos ylate 16-(p-toluensulfonyloxy)hexadecanol 1. Displacement of the tosyl group by thiocyanate followed by sodium borohydride reduction and sap onification afforded oligosaccharide 16-mercaptohexadecanyl glycosides that were isolated as the corresponding disulfides 6 and 17 unless ox ygen was rigorously excluded from the solvents used for work-up. Dithi othreitol reduction of disulfides and subsequent isolation under an in ert atmosphere with degassed solvents gave the thiols 7 and 18. Chemis orption of omega-glycosyl alkanethiols and alkanethiols onto gold elec trodes produces self-assembled monolayers that can act as amperometric biosensors for the detection of proteins that bind to the immobilized oligosaccharide epitope. (C) 1998 Elsevier Science Ltd. All rights re served.