Xylopyranoside-based agonists of D-myo-inositol 1,4,5-trisphosphate receptors: synthesis and effect of stereochemistry on biological activity.

@article{Rosenberg2001XylopyranosidebasedAO,
  title={Xylopyranoside-based agonists of D-myo-inositol 1,4,5-trisphosphate receptors: synthesis and effect of stereochemistry on biological activity.},
  author={H. Rosenberg and A. Riley and R. D. Marwood and V. Corr{\^e}a and C. Taylor and Potter BVL},
  journal={Carbohydrate research},
  year={2001},
  volume={332 1},
  pages={
          53-66
        }
}
  • H. Rosenberg, A. Riley, +3 authors Potter BVL
  • Published 2001
  • Chemistry, Medicine
  • Carbohydrate research
    • The synthesis of a series of tetrahydrofuranyl alpha- and beta-xylopyranoside trisphosphates, designed by excision of three motifs of adenophostin A is reported. The synthetic route features improved preparations of allyl alpha-D-xylopyranoside and its 2-O-benzyl ether, and gives access to four diastereoisomeric trisphosphates, which show a range of abilities to mobilise Ca2+ from the intracellular stores of hepatocytes. A comparison of the potencies of the four trisphosphates provides useful… CONTINUE READING
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    References

    SHOWING 1-10 OF 25 REFERENCES
    2-Hydroxyethyl-alpha-D-glucopyranoside-2,3',4'-trisphosphate, a novel, metabolically resistant, adenophostin A and myo-inositol-1,4,5-trisphosphate analogue, potently interacts with the myo-inositol-1,4,5-trisphosphate receptor.
    • 41
    C-glycoside based mimics of D-myo-inositol 1,4,5-trisphosphate.
    • 13
    Molecular recognition of adenophostin, a very potent Ca2+ inducer, at the D-myo-inositol 1,4,5-trisphosphate receptor.
    • 30
    Simplification of adenophostin A defines a minimal structure for potent glucopyranoside-based mimics of D-myo-inositol 1,4,5-trisphosphate.
    • 16
    Enantiomers of myo-inositol-1,3,4-trisphosphate and myo-inositol-1,4,6 -trisphosphate: stereospecific recognition by cerebellar and platelet myo-inositol-1,4,5-trisphosphate receptors.
    • 10
    Inframolecular Protonation Process of myo-Inositol 1,4,5-Tris(phosphate) and Related Compounds: Dynamics of the Intramolecular Interactions and Evidence of C−H···O Hydrogen Bonding
    • 32
    Synthesis and biological activities of inositol 1,4,5-trisphosphate mimics related to xylopyranosides
    • 28
    Inframolecular studies of the protonation of adenophostin A: comparison with 1-D-myo-inositol 1,4,5-trisphosphate.
    • 15
    Adenophostins A and B: potent agonists of inositol-1,4,5-trisphosphate receptor produced by Penicillium brevicompactum. Structure elucidation.
    • 48
    Disaccharide polyphosphates based upon adenophostin A activate hepatic D-myo-inositol 1,4,5-trisphosphate receptors.
    • 43