Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-α-D-glucosamine-O-methylglycoside acceptor
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Authors
Zhang, Xing
Dickinson, Demetria M.
Lin, Lei
Suflita, Matthew
Baytas, Sultan
Linhardt, Robert J.
Issue Date
2019-03-28
Type
Article
Language
ENG
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Alternative Title
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
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
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.
Publisher
Terms of Use
Journal
Volume
Issue
PubMed ID
DOI
ISSN
18733581
404039
404039