Synthesis and binding properties of cyclopentane analogues of myo-inositol 1,4,5-tris(phosphate)

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 P-31 NMR titration curves show that the tris(phosphate) 5 behaves as the superimposition of an independent phosphate and a vicinal bis(phosphate). (C) 2004 Elsevier Ltd. All rights reserved.