1D-myo-inositol 1,4,5-trisphosphate and 1D-myo-inositol 1,3,4,5-tetrakisphosphate analogues modified at C-3; synthesis of 1D-3-C-(trifluoromethyl)-myo-inositol 1,4,5-trisphosphate and 1L-chiro-insitol 1,2,3,5-tetrakisphosphate from L-quebrachitol

Abstract

The novel 3-modified 1D-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P₃] analogues 1D-3-C-(trifluoromethyl)-myo-inositol 1,4,5-trisphosphate and 1L-chiro-inositol 1,2,3,5-tetrakisphosphate are synthesized from L-quebrachitol, and the preliminary results on their Ca²⁺ releasing activity suggest that the Ins(1,4,5)P₃ receptor can accommodate some steric bulk in the axial region of the 3-position of Ins(1,4,5)P₃ when the equatorial 3-hydroxy group is retained.