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

Authors
Zhang, Xing
Dickinson, Demetria M.
Lin, Lei
Suflita, Matthew
Baytas, Sultan
Linhardt, Robert J.
ORCID
https://orcid.org/0000-0003-2219-5833
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Other Contributors
Issue Date
2019-03-28
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Degree
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Full Citation
Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-α-D-glucosamine-O-methylglycoside acceptor, X. Zhang, D. M. Dickinson, L. Lin, M. Suflita, S. Baytas, R. J. Linhardt, Tetrahedron Letters, 60, 911–915, 2019.
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.
Description
Tetrahedron Letters, 60, 911–915
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Department
The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
Publisher
Relationships
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Tetrahedron Letters
https://harc.rpi.edu/
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