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    Synthesis of a C-Glycoside Analog of sTn: an HIV and Tumor Associated Antigen

    Author
    Kuberan, Balagurunathan; Sikkander, Sulthan A.; Tomiyama, Hiroshi; Linhardt, Robert J.
    ORCID
    https://orcid.org/0000-0003-2219-5833
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    SYNTHESIS OF A C-GLYCOSIDE ANALOGUE OF STN AN HIV- AND.pdf (213.9Kb)
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    Date Issued
    2003-05-09
    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 a C-Glycoside Analog of sTn: an HIV and Tumor Associated Antigen, B. Kuberan, S.A. Sikkandar, H. Tomiyama, R.J. Linhardt, Angewandte Chemie, Intl.ed., 42, 2073-2074, 2003. (Full Text in PDF format)
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    URI
    https://hdl.handle.net/20.500.13015/5159; https://doi.org/10.1002/anie.200351099
    Abstract
    N-Acetylneuraminic acid occupies the nonreducing end of many naturally occurring glycoconjugates on the cell surface, including glycoproteins and glycolipids. The strategic location of glycoconjugates on the cell surface and the enormous structural information that they carry account for their major role in biological recognition in the control of both normal and pathological processes.[1] While the participation of sialic acid in these biological events has been established unequivocally in a large number of studies,[1] the linkage of sialic acid to glycoconjugates is one of the most labile glycosidic linkages, which renders these compounds less amenable to biological and biochemical studies.[2] Terminal sialic acid residues are easily cleaved in vitro under very mild acidic conditions and in vivo by neuraminidases.[3] The biological importance of sialic acid coupled with its lability towards hydrolysis prompted us to redesign the molecular architecture of glycoconjugates to afford a non-hydrolyzable glycosidic linkage to sialic acid. Such a stable linkage should contribute to our understanding of biological recognition and serve to enhance or suppress biological events at the molecular level. The replacement of the interglycosidic oxygen atom with a hydroxymethylene or methylene group affords a new class of hydrolytically stable C-glycoside analogues of glycoconjugates.[4] A method for the preparation of C-glycosides of ulosonic acids using SmI2 was pioneered in our laboratory.[5];
    Description
    Angewandte Chemie, Intl.ed., 42, 2073-2074; (Full Text in PDF format); 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
    Wiley
    Relationships
    The Linhardt Research Labs Online Collection; Rensselaer Polytechnic Institute, Troy, NY; Angewandte Chemie - International Edition; https://harc.rpi.edu/;
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    A full text version is available in DSpace@RPI;
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