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  • Tetrahydrofuran amino acids: Secondary structure in tetrameric and octameric carbopeptoids derived from a D-allo 5-(aminomethyl)tetrahydrofuran-2-carboxylic acid.

    Author(s)
    Hungerford, Natasha Lynn
    Claridge, Timothy D. W.
    Watterson, Mark P.
    Aplin, Robin T.
    Moreno, Andres
    Fleet, George W. J.
    Griffith University Author(s)
    Hungerford, Natasha L.
    Year published
    2000
    Metadata
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    Abstract
    The synthesis of a D-allo-5-(azidomethyl)tetrahydrofuran-2-carboxylate as an amino acid precursor (in which the carboxylic acid is cis to the azidomethyl substituent and trans to the diol moiety) is reported from D-ribose. The oligomerisation of this monomer to dimeric, tetrameric and octameric carbopeptoids is described. NMR studies into the solution structures of cyclohexylidene-protected oligomers and of a deprotected tetramer with eight free hydroxy groups are described.The synthesis of a D-allo-5-(azidomethyl)tetrahydrofuran-2-carboxylate as an amino acid precursor (in which the carboxylic acid is cis to the azidomethyl substituent and trans to the diol moiety) is reported from D-ribose. The oligomerisation of this monomer to dimeric, tetrameric and octameric carbopeptoids is described. NMR studies into the solution structures of cyclohexylidene-protected oligomers and of a deprotected tetramer with eight free hydroxy groups are described.
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    Journal Title
    Journal of the Chemical Society, Perkin Transactions 1
    Volume
    2000
    DOI
    https://doi.org/10.1039/B002996N
    Subject
    Organic Chemical Synthesis
    Medicinal and Biomolecular Chemistry
    Organic Chemistry
    Publication URI
    http://hdl.handle.net/10072/60511
    Collection
    • Journal articles

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