Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-α-d-glucosamine-O-methylglycoside acceptor. Issue 13 (28th March 2019)

• Record Type: Journal Article
• Authors: Zhang, Xing; Dickinson, Demetria M.; Lin, Lei; Suflita, Matthew; Baytas, Sultan; Linhardt, Robert J.
• Is Part Of: Tetrahedron letters. Volume 60:Issue 13(2019)
• Page Start: 911
• Page End: 915
• Publication Date: 2019-03-28
• Subjects: Chemoenzymatic synthesis -- Oligosaccharides, glycosylation -- Heparin -- Heparan sulfate; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.02.036
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Chemoenzymatic synthesis of heparan sulfate tetrasaccharide. Enzyme-catalyzed glycosylation of monosaccharide acceptor. Method for chemoenzymatic synthesis of fonaparinux analogs. Abstract: Heparan sulfate tetrasaccharide2 was efficiently prepared in seven steps through chemoenzymatic synthesis. A monosaccharide5, 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 acceptor3, greatly simplifying the route to tetrasaccharide target2 . This approach provides a critical tetrasaccharide intermediate for subsequent chemoenzymatic transformation to fondaparinux and its analogues.