SYNTHESIS OF 1-O-ALKYL-MYO-INOSITOL 3,4,5-TRISPHOSPHATES AND 1-O-ACYL-MYO-INOSITOL 3,4,5-TRISPHOSPHATES AS NOVEL ANALOGS OF PHOSPHATIDYL-MYO-INOSITOL 3,4,5-TRISPHOSPHATE
T. Sawada et al., SYNTHESIS OF 1-O-ALKYL-MYO-INOSITOL 3,4,5-TRISPHOSPHATES AND 1-O-ACYL-MYO-INOSITOL 3,4,5-TRISPHOSPHATES AS NOVEL ANALOGS OF PHOSPHATIDYL-MYO-INOSITOL 3,4,5-TRISPHOSPHATE, Bioorganic & medicinal chemistry letters, 5(19), 1995, pp. 2263-2266
Homochiral 1-O-alkyl and 1-O-acyl derivatives of myo-inositol 3,4,5-tr
isphosphate were designed and synthesized as novel analogues of phosph
atidyl-myo-inositol 3,4,5-trisphosphate. 1-O-Octadecyl and 1-O-stearoy
l analogues inhibited the synthesis of phosphatidyl-myo-inositol 3,4-b
isphosphate from phosphatidyl-myo-inositol 3,4,5-trisphosphate catalyz
ed by PIns-3,4,5-P-3 5-phosphatase. These compounds may act as competi
tors in the enzyme reaction, suggesting that they may be useful in stu
dies of the role of phosphatidyl-myo-inositol 3,4,5-trisphosphate as a
candidate second messenger in cellular signal transduction.