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).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adrenal Cortex / ultrastructure
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Animals
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Calcium / metabolism
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Calcium Channels / metabolism
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Cattle
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Cell Line
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Endoplasmic Reticulum / metabolism
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In Vitro Techniques
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Inositol 1,4,5-Trisphosphate / analogs & derivatives*
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Inositol 1,4,5-Trisphosphate / chemical synthesis*
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Inositol 1,4,5-Trisphosphate / chemistry
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Inositol 1,4,5-Trisphosphate / metabolism*
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Inositol 1,4,5-Trisphosphate / pharmacology
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Inositol 1,4,5-Trisphosphate Receptors
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Microsomes / drug effects
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Microsomes / metabolism
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Molecular Conformation
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Pancreas / cytology
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Permeability
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Purines / chemical synthesis*
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Purines / chemistry
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Purines / pharmacology
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Radioligand Assay
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Receptors, Cytoplasmic and Nuclear / agonists*
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Receptors, Cytoplasmic and Nuclear / metabolism
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Stereoisomerism
Substances
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2-O-(4'-(N-9''-purinyl)butyl) myo-inositol 1,4,5-tris(phosphate)
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Calcium Channels
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Inositol 1,4,5-Trisphosphate Receptors
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Purines
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Receptors, Cytoplasmic and Nuclear
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Inositol 1,4,5-Trisphosphate
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Calcium