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Analysis of Fucosylated Human Milk Trisaccharides in Biotechnological Context Using Genetically Encoded Biosensors
Published on: April 13, 2019
Rapid Access to Human Milk Oligosaccharide Analogues through a Partially Protected N-Acetylglucosamine Donor
Qing Wang1,2, Qian Zhang1,3, Liran Yang1,3
1School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, China.
Abstract:
Access to structurally defined human milk oligosaccharides (HMOs) remains nontrivial because chemical synthesis often relies on extensive protecting-group manipulations. Here, we report a gold(I)-catalyzed, protecting-group-minimized approach to HMO-related tri- and tetrasaccharides using a partially protected 2-acetamido-2-deoxy glycosyl donor. Efficient formation of the β-GlcNAc-(1→3)-Gal motif was found to depend strongly on the protecting-group pattern of the galactosyl acceptor, with a 2-O-benzyl group being crucial for productive glycosylation. Subsequent Au(I)-catalyzed site-selective 3'-O-glycosylation and further reducing-end elaboration enabled rapid diversification of the core disaccharide.
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