Chemical O-sulfation of N-sulfoheparosan: A route to rare N-sulfo-3-O-sulfoglucosamine and 2-O-sulfoglucuronic acid

Yan, Lufeng
Brodfueher, Paul
Fu, Li
Zhang, Fuming
Chen, Shiguo
Dordick, Jonathan S.
Linhardt, Robert J.
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Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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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.
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.
Glycoconjugate Journal, 37, 589–597
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The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Glycoconjugate Journal