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    Helix-forming carbohydrate amino acids

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    Authors
    Claridge, Timothy D.W.
    Long, Daniel D.
    Baker, Christopher M.
    Odell, Barbara
    Grant, Guy H.
    Edwards, Alison A.
    Tranter, George E.
    Fleet, George W.J.
    Smith, Martin D.
    Issue Date
    2005
    
    Metadata
    Show full item record
    Abstract
    The solution-phase conformational properties of tetrameric and octameric chains of C-glycosyl α-d-lyxofuranose configured tetrahydrofuran amino acids (where the C-2 and C-5 substituents on the tetrahydrofuran ring are trans to each other) were examined using NMR and IR and CD in organic solvents. Studies by NMR and IR demonstrated that in chloroform solution, the tetramer 7 does not adopt a hydrogen-bonded conformation whereas the octamer 10 populates a well-defined helical secondary structure stabilized by 16-membered (i, i − 3) interresidue hydrogen bonds, similar to a π-helix. Circular dichroism studies in trifluoroethanol are consistent with this conformation for the octamer 10, and also indicate that the tetramer 7 adopts a rigid conformation not stabilized by hydrogen bonds.
    Citation
    Claridge, T.D.W., Long, D.D., Baker, C.M., Odell, B., Grant, G.H., Edwards, A.A., Tranter, G.E., Fleet, G.W.J., Smith, M.D. (2005) 'Helix-Forming carbohydrate amino acids', Journal of Organic Chemistry, 70(6), pp.2082-2090.
    Publisher
    American Chemical Society
    Journal
    The Journal of Organic Chemistry
    URI
    http://hdl.handle.net/10547/294638
    DOI
    10.1021/jo0480040
    Additional Links
    http://pubs.acs.org/doi/abs/10.1021/jo0480040
    Type
    Article
    Language
    en
    ISSN
    0022-3263
    1520-6904
    ae974a485f413a2113503eed53cd6c53
    10.1021/jo0480040
    Scopus Count
    Collections
    Cell and Cryobiology Research Group

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