Chemical O-sulfation of N-sulfoheparosan: A route to rare N-sulfo-3-O-sulfoglucosamine and 2-O-sulfoglucuronic acid
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Authors
Yan, Lufeng
Brodfueher, Paul
Fu, Li
Zhang, Fuming
Chen, Shiguo
Dordick, Jonathan S.
Linhardt, Robert J.
Issue Date
2020-10-01
Type
Article
Language
ENG
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Alternative Title
Abstract
Heparosan, the capsular polysaccharide of E. coli K5 is currently used as the starting material in the chemoenzymatic synthesis of heparan sulfate and the structurally related anticoagulant drug heparin. Base hydrolysis of N-acetyl groups and their subsequent N-sulfonation, are used to prepare N-sulfoheparosan an intermediate of biosynthesis. In the present study, when excess sulfonation reagent was used during N-sulfonation, some O-sulfation also took place in the N-sulfoheparosan product. After a nearly full digestion, a hexasaccharide fraction exhibited resistance to heparin lyase II. Excessive digestion by heparin lyase II and structural identification by NMR and mass spectroscopy indicated that the resistant hexasaccharide fraction has two structures, ΔUA-GlcNS-GlcA2S-GlcNS-GlcA-GlcNS and ΔUA-GlcNS-GlcA- GlcNS3S-GlcA-GlcNS in similar amounts. The 2-sulfated structure exhibited partial resistance to heparin lyase II; however the structure of ΔUA-GlcNS-GlcA-GlcNS3S was completely resistant to heparin lyase II.
Description
Glycoconjugate Journal, 37, 589–597
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
Chemical O-sulfation of N-sulfoheparosan: A route to rare N-sulfo-3-O-sulfoglucosamine and 2-O-sulfoglucuronic acid, L. Yan, P. Brodfueher, L. Fu, F. Zhang, S. Chen, J. S. Dordick, R. J. Linhardt, Glycoconjugate Journal, 37, 589–597, 2020.
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Volume
Issue
PubMed ID
DOI
ISSN
15734986
2820080
2820080