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  • A Versatile Synthetic Approach toward Diversity Libraries using Monosaccharide Scaffolds

    Author(s)
    Le Thanh, Giang
    Abbenante, Giovanni
    Adamson, George
    Becker, Bernd
    Clark, Chris
    Condie, Glenn
    Falzun, Tania
    Grathwohl, Matthias
    Gupta, Praveer
    Hanson, Michael
    Huynh, Ngoc
    Katavic, Peter
    Kuipers, Krystle
    Lam, Ann
    Liu, Ligong
    Mann, Maretta
    Mason, Jeff
    McKeveney, Declan
    Muldoon, Craig
    Pearson, Andrew
    Rajaratnam, Premraj
    Ryan, Sarah
    Tornetzki, Gerry
    Verquin, Geraldine
    Waanders, Jennifer
    West, Michael
    Wilcox, Neil
    Wimmer, Norbert
    Yau, Annika
    Zuegg, Johannes
    Meutermans, Wim
    Griffith University Author(s)
    Huynh, Ngoc
    Pearson, Andrew G.
    Katavic, Peter
    Year published
    2010
    Metadata
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    Abstract
    The pyranose scaffold is unique in its ability to position pharmacophore substituents in various ways in 3D space, and unique pharmacophore scanning libraries could be envisaged that focus on scanning topography rather than diversity in the type of substituents. Approaches have been described that make use of amine and acid functionalities on the pyranose scaffolds to append substituents, and this has enabled the generation of libraries of significant structural diversity. Our general aim was to generate libraries of pyranose-based drug-like mimetics, where the substituents are held close to the scaffold, in order to obtain ...
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    The pyranose scaffold is unique in its ability to position pharmacophore substituents in various ways in 3D space, and unique pharmacophore scanning libraries could be envisaged that focus on scanning topography rather than diversity in the type of substituents. Approaches have been described that make use of amine and acid functionalities on the pyranose scaffolds to append substituents, and this has enabled the generation of libraries of significant structural diversity. Our general aim was to generate libraries of pyranose-based drug-like mimetics, where the substituents are held close to the scaffold, in order to obtain molecules with better defined positions for the pharmacophore substituents. Here we describe the development of a versatile synthetic route toward peptide mimetics build on 2-amino pyranose scaffolds. The method allows introduction of a wide range of substituent types, it is regio- and stereospecific, and the later diversity steps are performed on solid phase. Further, the same process was applied on glucose and allose scaffolds, in the exemplified cases, and is likely adaptable to other pyranose building blocks. The methods developed in this work give access to molecules that position the three selected binding elements in various 3D orientations on a pyranose scaffold and have been applied for the production of a systematically diverse library of several hundred monosaccharide-based mimetics.
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    Journal Title
    Journal of Organic Chemistry
    Volume
    75
    Issue
    1
    DOI
    https://doi.org/10.1021/jo9021919
    Subject
    Organic Chemical Synthesis
    Medicinal and Biomolecular Chemistry
    Organic Chemistry
    Publication URI
    http://hdl.handle.net/10072/157502
    Collection
    • Journal articles

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