Simplifying Oligosaccharide Synthesis: Efficient Synthesis of Lactosamine and Siaylated Lactosamine Oligosaccharide Donors
- 21 February 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (6), 2426-2431
- https://doi.org/10.1021/jo026569v
Abstract
A practical sequence is described for converting d-glucosamine into peracetylated Gal(β-1,4)GlcNTroc(β1-S)Ph and Neu5Ac(α-2,3)Gal(β-1,4)GlcNTroc(β1-S)Ph building blocks using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis. The known trichloroethoxycarbonyl, N-Troc, protecting group was selected as a suitable protecting group for both enzymatic and chemical reaction conditions. These oligosaccharide building blocks proved effective donors for the β-selective glycosylation of the unreactive OH-3 of a polymeric PEG-bound acceptor and for the axial OH-2 of a mannose acceptor in good yields. The resulting complex oligosaccharides are useful for vaccine and pharmaceutical applications.Keywords
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