Synthesis of (+/-)-2-O-[4'-(N-9'-purinyl)butyl] myo-inositol 1,4,5-tris(phosphate), a potent full agonist at the D-myo-inositol 1,4,5-tris(phosphate) receptor |
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| Authors: | Moris Marc-Antoine Caron Annabelle Z Guillemette Gaétan Rognan Didier Schmitt Martine Schlewer Gilbert |
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| Affiliation: | Laboratoire de Pharmacochimie de la Communication Cellulaire UMR 7081 du CNRS, Faculté de Pharmacie, Université Louis Pasteur de Strasbourg, 74, route du Rhin, 67401 Illkirch, France. |
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| Abstract: | Racemic 2-O-[4'(9'-N-purinyl)butyl] myo-inositol 1,4,5-tris(phosphate) 8 was synthesized starting from myo-inositol. Substitution of position 2 by an alkyl side chain was rendered possible by inversion of the chair conformation of the inositol ring by means of an orthoester. The final compound is a full agonist with the same order of potency as d-myo-inositol 1,4,5-tris(phosphate). |
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