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  • Combinatorial Chemoenzymatic Synthesis and High-throughput Screening of Sialosides

    Author(s)
    Chokhawala, Harshal A.
    Huang, Shengshu
    Lau, Kam
    Yu, Hai
    Cheng, Jiansong
    Thon, Vireak
    Hurtado-Ziola, Nancy
    Guerrero, Juan A.
    Varki, Ajit
    Chen, Xi
    Griffith University Author(s)
    Huang, Shengshu
    Year published
    2008
    Metadata
    Show full item record
    Abstract
    Although the vital roles of structures containing sialic acid in biomolecular recognition are well documented, limited information is available on how sialic acid structural modifications, sialyl linkages, and the underlying glycan structures affect the binding or the activity of sialic acid-recognizing proteins and related downstream biological processes. A novel combinatorial chemoenzymatic method has been developed for the highly efficient synthesis of biotinylated sialosides containing different sialic acid structures and different underlying glycans in 96-well plates from biotinylated sialyltransferase acceptors and ...
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    Although the vital roles of structures containing sialic acid in biomolecular recognition are well documented, limited information is available on how sialic acid structural modifications, sialyl linkages, and the underlying glycan structures affect the binding or the activity of sialic acid-recognizing proteins and related downstream biological processes. A novel combinatorial chemoenzymatic method has been developed for the highly efficient synthesis of biotinylated sialosides containing different sialic acid structures and different underlying glycans in 96-well plates from biotinylated sialyltransferase acceptors and sialic acid precursors. By transferring the reaction mixtures to NeutrAvidin-coated plates and assaying for the yields of enzymatic reactions using lectins recognizing sialyltransferase acceptors but not the sialylated products, the biotinylated sialoside products can be directly used, without purification, for high-throughput screening to quickly identify the ligand specificity of sialic acid-binding proteins. For a proof-of-principle experiment, 72 biotinylated a2,6-linked sialosides were synthesized in 96-well plates from 4 biotinylated sialyltransferase acceptors and 18 sialic acid precursors using a one-pot three-enzyme system. High-throughput screening assays performed in NeutrAvidin-coated microtiter plates show that whereas Sambucus nigra Lectin binds to a2,6-linked sialosides with high promiscuity, human Siglec-2 (CD22) is highly selective for a number of sialic acid structures and the underlying glycans in its sialoside ligands.
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    Journal Title
    ACS Chemical Biology
    Volume
    3
    Issue
    9
    DOI
    https://doi.org/10.1021/cb800127n
    Copyright Statement
    Self-archiving of the author-manuscript version is not yet supported by this journal. Please refer to the journal link for access to the definitive, published version or contact the authors for more information.
    Subject
    Organic Chemical Synthesis
    Chemical Sciences
    Biological Sciences
    Publication URI
    http://hdl.handle.net/10072/38543
    Collection
    • Journal articles

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