Synthesis of adenophostin A and congeners modified at glucose

@article{Marwood2000SynthesisOA,
  title={Synthesis of adenophostin A and congeners modified at glucose},
  author={R. D. Marwood and A. Riley and D. Jenkins and B. L. Potter},
  journal={Journal of The Chemical Society-perkin Transactions 1},
  year={2000},
  pages={1935-1947}
}
  • R. D. Marwood, A. Riley, +1 author B. L. Potter
  • Published 2000
  • Chemistry
  • Journal of The Chemical Society-perkin Transactions 1
    • A convergent route is described to the super-potent 1D-myo-inositol 1,4,5-trisphosphate receptor agonist adenophostin A (2) and analogues 5 and 7, in which the glucose bisphosphate unit is replaced by corresponding xylose bisphosphate and mannose bisphosphate units respectively. Adenosine was converted into its 2′,3′-O-p-methoxybenzylidene derivative 8ab, which was selectively N6-dimethoxytritylated by a transient protection method. 5′-O-Benzylation followed by reductive acetal cleavage gave… CONTINUE READING
    View via Publisher
    15 Citations
    15 Citations
    Citation Type

    Citation Type

    Total synthesis of nucleobase-modified adenophostin A mimics.
    • 13
    Adenophostins: High-Affinity Agonists of IP(3) Receptors.
    • 19
    Structural determinants of adenophostin A activity at inositol trisphosphate receptors.
    • 45
    • PDF
    Designing an effective approach for obtaining methylenecarboxylate analogues of adenophostin A. Preliminary results.
    • 4
    Conformational and inframolecular studies of the protonation of adenophostin analogues lacking the adenine moiety.
    Synthesis of disaccharide nucleosides by the O-glycosylation of natural nucleosides with thioglycoside donors.
    • 5
    • PDF
    Stimulation of Inositol 1,4,5-Trisphosphate (IP3) Receptor Subtypes by Adenophostin A and Its Analogues
    • 10
    • PDF
    Glycosylation using hemiacetal sugar derivatives: Synthesis of O-α-D-rhamnosyl-(1 → 3)-O-α-D-rhamnosyl-(1 → 2)-D-rhamnose and O-α-D-tyvelosyl-(1 → 3)-O-α-D-mannosyl-(1 → 4)-L-rhamnose
    • 6
    New Sugar‐Based Permeant Analogs of D‐Myo‐Inositol 1,4,5‐Trisphosphate Mimicking the Effect of Vasopressin: Synthesis and Biologic Evaluation
    • 3
    Comparative investigations on the regioselective mannosylation of 2,3,4-triols of mannose
    • 15

    References

    SHOWING 1-10 OF 54 REFERENCES
    SYNTHESIS OF 2',3 ,4 -TRISPHOSPHATE-CONTAINING ANALOGS OF ADENOPHOSTIN A
    • 15
    An expeditious route to the synthesis of adenophostin A
    • 25
    SYNTHESIS OF 3 ,4 -BISPHOSPHATE-CONTAINING ANALOGS OF ADENOPHOSTIN A
    • 14
    A Ca(2+)-mobilising carbohydrate-based polyphosphate: synthesis of 2-hydroxyethyl alpha-D-glucopyranoside 2',3,4-trisphosphate.
    • 28
    Synthesis of a hexasaccharide acceptor corresponding to the reducing terminus of mycobacterial 3-O-methylmannose polysaccharide (MMP).
    • 13
    • PDF
    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
    SYNTHESIS OF ADENOPHOSTIN ANALOGUES LACKING THE ADENINE MOIETY AS NOVEL POTENT IP3 RECEPTOR LIGANDS : SOME STRUCTURAL REQUIREMENTS FOR THE SIGNIFICANT ACTIVITY OF ADENOPHOSTIN A
    • 37
    Unambiguous total synthesis of the enantiomers of myo-inositol 1,3,4-trisphosphate: 1L-myo-inositol 1,3,4-trisphosphate mobilizes intracellular Ca2+ in Limulus photoreceptors.
    • 19
    Disaccharide polyphosphates based upon adenophostin A activate hepatic D-myo-inositol 1,4,5-trisphosphate receptors.
    • 43
    Adenophostins A and B: potent agonists of inositol-1,4,5-trisphosphate receptor produced by Penicillium brevicompactum. Structure elucidation.
    • 48