Synthesis of a Disaccharide with a Thiol Spacer Used in Gold Nanoparticles
The synthesis of a mannose-bearing disaccharide containing a thiol spacer at the reducing end was carried out to provide a tethered sugar suitable for attaching to gold nanoparticles. Such sugar is designed to mimic carbohydrates involved in cell-surface interactions. The molecule was constructed via Schmidt glycosylation of an appropriately protected glycosyl donor and an acceptor, followed by removal of protective groups and reductive amination to introduce a protected thiol spacer at the reducing end of the glycan. Subsequent removal of the thiol protective group gave the target disaccharide in a satisfactory yield.
Helen Zhang, David Jin and X.J. Zhao
C. Wang, "Synthesis of a Disaccharide with a Thiol Spacer Used in Gold Nanoparticles", Advanced Materials Research, Vol. 643, pp. 153-156, 2013