Rapid Access to Human Milk Oligosaccharide Analogues through a Partially Protected N -Acetylglucosamine Donor
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.
Fields of Study & Subjects
Carbohydrate Chemistry and Synthesis
Glycosylation and Glycoproteins Research
Infant Nutrition and Health
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 23
- Pages
- 7191–7195
- Publication date
- 28 May 2026
- Language
- EN