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

    Author
    Yan, Lufeng; Brodfueher, Paul; Fu, Li; Zhang, Fuming; Chen, Shiguo; Dordick, Jonathan S.; Linhardt, Robert J.
    ORCID
    https://orcid.org/0000-0003-2219-5833
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    Other Contributors
    Date Issued
    2020-10-01
    Subject
    Biology; Chemistry and chemical biology; Chemical and biological engineering; Biomedical engineering
    Degree
    Terms of Use
    In Copyright : this Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). https://rightsstatements.org/page/InC/1.0/;
    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.
    Metadata
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    URI
    https://doi.org/10.1007/s10719-020-09939-7; https://hdl.handle.net/20.500.13015/5482
    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.
    Department
    The Linhardt Research Labs.; The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS);
    Relationships
    The Linhardt Research Labs Online Collection; Rensselaer Polytechnic Institute, Troy, NY; Glycoconjugate Journal; https://harc.rpi.edu/;
    Access
    https://login.libproxy.rpi.edu/login?url=https://doi.org/10.1007/s10719-020-09939-7;
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