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    Synthesis of nor-C-linked neuraminic acid disaccharide: A versatile precursor of C-analogs of oligosialic acids and gangliosides

    Author
    Yuan, Xuejun; Ress, Dino K.; Linhardt, Robert J.
    ORCID
    https://orcid.org/0000-0003-2219-5833
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    SYNTHESIS OF NOR-C-LINKED NEURAMINIC ACID DISACCHARIDE.pdf (1.155Mb)
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    Date Issued
    2007-04-13
    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
    Synthesis of nor-C-linked neuraminic acid disaccharide: A versatile precursor of C-analogs of oligosialic acids and gangliosides, X. Yuan, D. K. Ress, R. J. Linhardt, Journal of Organic Chemistry, 72, 3085-3088, 2007.
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    URI
    https://hdl.handle.net/20.500.13015/5204; https://doi.org/10.1021/jo0623787
    Abstract
    The Neu5Acalpha(2,8)Neu5Ac disaccharide is an important constituent of tumor related antigen, however, the O-linkage is catabolically unstable. Vaccination with a catabolically stable sialic acid C-glycoside analog might enhance immunogenicity. The synthesis of Neu5Ac nor-C-disaccharide 20R/S, corresponding to versatile precursors of C-analogs of oligosialic acid and gangliosides, is reported. The synthesis of the protected acceptor was not straightforward, as ester, silyl ether, and isopropylidene protection failed to afford desired C-linked disaccharide. Allyl ether protection of hydroxyl groups and acetyl protection of the acetamido facilitated the successful synthesis of the 8-aldehyde neuraminyl acceptor. Samarium mediated C-glycosylation afforded the desired nor-C-disaccharide as a mixture of two separable diastereomers.;
    Description
    Journal of Organic Chemistry, 72, 3085-3088; 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
    American Chemical Society (ACS)
    Relationships
    The Linhardt Research Labs Online Collection; Rensselaer Polytechnic Institute, Troy, NY; Journal of Organic Chemistry; https://harc.rpi.edu/;
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    A full text version is available in DSpace@RPI;
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