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Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-α-d-glucosamine-O-methylglycoside acceptor

Author:
Zhang, Xing, Dickinson, Demetria M., Lin, Lei, Suflita, Matthew, Baytas, Sultan, Linhardt, Robert J.
Source:
Tetrahedron letters 2019
ISSN:
0040-4039
Subject:
chemical structure, enzymes, glycosylation, heparan sulfate, organic compounds
Abstract:
Heparan sulfate tetrasaccharide 2 was efficiently prepared in seven steps through chemoenzymatic synthesis. A monosaccharide 5, N-acetyl-α-d-glucosamine- O-methylglycoside (GlcNAc-OMe), was successfully used as an acceptor in a heparosan synthase (pmHS2)-catalyzed glycosylation reaction. This avoided the multi-step synthesis of a more complex disaccharide acceptor 3, greatly simplifying the route to tetrasaccharide target 2. This approach provides a critical tetrasaccharide intermediate for subsequent chemoenzymatic transformation to fondaparinux and its analogues.
Agid:
6345551