Synthesis of a Mannose-Bearing Disaccharide with a Thiol Spacer at the Reducing End

Author(s): Chao Wang, David C. Baker

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 5 , 2011

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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. An array of such sugars 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. A new finding that the anomeric reductive amination is capable of concomitantly removing a neighboring N-acetyl group was also observed. Subsequent removal of the thiol protective group and purification of the product gave the target disaccharide in a satisfactory yield.

Keywords: Carbohydrate, oligosaccharide, glycosylation, mannose, nanoparticle, thiol, biomineralization, cytotoxicity, globular

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Article Details

Year: 2011
Page: [295 - 300]
Pages: 6
DOI: 10.2174/157017811795685090
Price: $65

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