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Structural determinants of adenophostin A activity at inositol trisphosphate receptors.
Adenophostin A is the most potent known agonist of inositol 1,4,5-trisphosphate (InsP(3)) receptors. Ca(2+) release from permeabilized hepatocytes was 9.9 +/- 1.6-fold more sensitive to adenophostinExpand
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Synthesis of adenophostin A
Abstract The natural product and potent agonist of the d - myo -inositol 1,4,5-trisphosphate receptor, adenophostin A, was synthesised from adenosine and d -glucose using efficient methodology. TheExpand
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Simplification of adenophostin A defines a minimal structure for potent glucopyranoside-based mimics of D-myo-inositol 1,4,5-trisphosphate.
The synthesis of 1-O-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-alpha-D-glucopyranosid e 3,4,3'-trisphosphate (7), a novel Ca2+ mobilising agonist at the Ins(1,4,5)P3 receptor, designed by excision ofExpand
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Contribution of the adenine base to the activity of adenophostin A investigated using a base replacement strategy.
Syntheses of 3'-O-alpha-D-glucopyranosyl-1-beta-D-ribofuranosidoimidazole 2',3'', 4''-trisphosphate (7) and 3'-O-alpha-D-glucopyranosyl-9-beta-D-ribofuranosidopurine 2',3'',4''- trisphosphate (8),Expand
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Interactions of Inositol 1,4,5-Trisphosphate (IP3) Receptors with Synthetic Poly(ethylene glycol)-linked Dimers of IP3 Suggest Close Spacing of the IP3-binding Sites*
The distances between the inositol 1,4,5-trisphosphate (IP3)-binding sites of tetrameric IP3 receptors were probed using dimers of IP3linked by poly(ethylene glycol) (PEG) molecules of differingExpand
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Synthesis of potent agonists of the D-myo-inositol 1,4, 5-trisphosphate receptor based on clustered disaccharide polyphosphate analogues of adenophostin A.
Clustered disaccharide analogues of adenophostin A (2), i.e. mono-, di-, and tetravalent derivatives 6-8, respectively, were synthesized and evaluated as novel ligands for the tetramericExpand
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C-glycoside based mimics of D-myo-inositol 1,4,5-trisphosphate.
Epimeric C-glycoside based polyphosphates, alpha- and beta-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allylExpand
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Xylopyranoside-based agonists of D-myo-inositol 1,4,5-trisphosphate receptors: synthesis and effect of stereochemistry on biological activity.
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 improvedExpand
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Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: synthesis and biological activity.
The high affinity of adenophostin A for 1D-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P(3)] receptors may be related to an alteration in the position of its 2'-phosphate group relative to theExpand
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