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    Enzymatic Preparation of Heparin Oligosaccharides Containing Antithrombin III Binding Sites

    Author
    Toida, Toshihiko; Hileman, Ronald E.; Smith, April E.; Vlahova, Petinka I.; Linhardt, Robert J.
    ORCID
    https://orcid.org/0000-0003-2219-5833
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    ENZYMATIC PREPARATION OF HEPARIN OLIGOSACCHARIDES CONTAINING ANTITHROMBIN III BINDING SITES.pdf (379.3Kb)
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    Date Issued
    1996-12-30
    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
    Enzymatic Preparation of Heparin Oligosaccharides Containing Antithrombin III Binding Sites, T. E. Toida, R. E. Hileman, A. E. Smith, P. I. Vlahova, R.J. Linhardt, Journal of Biological Chemistry, 271, 32040-32047, 1996.
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    URI
    https://hdl.handle.net/20.500.13015/5162; https://doi.org/10.1074/jbc.271.50.32040
    Abstract
    Two new oligosaccharides were prepared from heparin by its partial depolymerization using heparin lyase I (EC 4.2.2.7) in an attempt to prepare oligosaccharides having intact antithrombin III binding sites. The oligosaccharides were purified by chromatography on the basis of both size and charge and demonstrated a high level of purity by capillary electrophoresis. One- and two-dimensional 1H NMR spectroscopy at 500 MHz revealed the structure of each oligosaccharide. The octasaccharide and decasaccharide are ΔUAp2S(1→4)-α-DGlcNpS6S(1→4)-α-L-IdoAp(1→4)-α-D-GlcNpAc6S(1→4)-βD-GlcAp(1→4)-α-D-GlcNpS3S6S(1→4)-α-L-IdoAp2S(1→4)α-D-GlcNpS6S (where ΔUAp is 4-deoxy-α-L-threo-hex-enopyranosyluronic acid, GlcNp is 2-amino-2-deoxy-glucopyranose, GlcAp is glucopyranosyluronic acid, S is sulfate and Ac is acetate) and ΔUAp2S(1→4)-α-D-GlcNpS6S(1→4)-α-L-IdoAp(1→4)-α-D-GlcNpAc6S (1→4)-β-D-GlcAp(1→4)-α-D-GlcNpS3S6S(1→4)-α-L-IdoAp2S(1→4)-α-D-GlcNpS6S(1→4)-α-L-IdoAp2S(1→4)-α-D-GlcNpS6S, respectively. A hexasaccharide containing a similar structural motif to that found in the antithrombin III binding site and having greatly reduced anticoagulant activity was also isolated. The structure of the hexasaccharide is ΔUAp2S(1→4)-α-D-GlcNpAc6S(1→4)-β-D-GlcAp(1→4)-α-D-GlcNpS3S6S(1→4)-α-L-IdoAp(1→4)-α-D-GlcNpS6S. The octasaccharide and decasaccharide correspond to the predominant structural motif found in porcine intestinal mucosal heparin. Sufficient quantities of the decasaccharide were obtained to examine its interaction with antithrombin III using microtitration calorimetry. This decasaccharide bound to antithrombin III with similar avidity as heparin and showed comparable anticoagulant activity, as determined using an antithrombin III dependent anti-factor Xa assay. Interestingly, while both decasaccharide and heparin bound to antithrombin with nanomolar affinity, very little heat of binding was observed.;
    Description
    Journal of Biological Chemistry, 271, 32040-32047; 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);
    Publisher
    Elsevier
    Relationships
    The Linhardt Research Labs Online Collection; Rensselaer Polytechnic Institute, Troy, NY; Journal of Biological Chemistry; https://harc.rpi.edu/;
    Access
    Open Access; A full text version is available in DSpace@RPI;
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