title: Synthesis and binding properties of cyclopentane analogues of myo-inositol 1,4,5-tris(phosphate).
abstract: Cyclopentanic analogues of myo-inositol 1,4,5-tris(phosphate) were synthesised starting from cyclopentadiene. The affinities of the trisphosphorylated derivatives for the Ins(1,4,5)P(3) receptors were equipotent to that of compound 4, showing that the relative orientation of the functional groups, particularly of the hydroxyl, is not of prime importance in this series. The (31)P NMR titration curves show that the tris(phosphate) 5 behaves as the superimposition of an independent phosphate and a vicinal bis(phosphate).
authors.affiliation: Laboratoire de Pharmacochimie de la Communication Cellulaire UMR 7081 du CNRS, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch, France.
authors.forename: Marc-Antoine
authors.initials: MA
authors.lastname: Moris
authors.forename: Annabelle Z
authors.initials: AZ
authors.lastname: Caron
authors.forename: Gaétan
authors.initials: G
authors.lastname: Guillemette
authors.forename: Gilbert
authors.initials: G
authors.lastname: Schlewer
mesh_terms: D000302:Adrenal Cortex / Q000648:ultrastructure; D000818:Animals; D001667:Binding, Competitive; D015220:Calcium Channels / Q000378:metabolism; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D015544:Inositol 1,4,5-Trisphosphate / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D053496:Inositol 1,4,5-Trisphosphate Receptors; D009682:Magnetic Resonance Spectroscopy; D008861:Microsomes / Q000378:metabolism; D015394:Molecular Structure; D018160:Receptors, Cytoplasmic and Nuclear / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D015220:Calcium Channels; D003517:Cyclopentanes; D053496:Inositol 1,4,5-Trisphosphate Receptors; D018160:Receptors, Cytoplasmic and Nuclear; D015544:Inositol 1,4,5-Trisphosphate