myo-Inositol phosphorothioates, phosphatase-resistant analogues of myo-inositol phosphates. Synthesis of DL-myo-inositol 1,4-bisphosphate and DL-myo-inositol 1,4-bisphosphorothioate.
Syntheses of a metabolite of the second messenger myo-inositol 1,4,5-trisphosphate, myo-inositol 1,4-bisphosphate, and an analogue, the 1,4-bisphosphorothioate, are reported, by using phosphite chemistry on (+/-)-1,2:4,5-di-isopropylidene-myo-inositol. The synthesis of (+/-)-1,2:4,5-di-isopropylidene 3,6-bis[di-(2-cyanoethyl)]phosphite provides an intermediate that can be oxidized to either the corresponding bisphosphate or bisphosphorothioate. myo-Inositol phosphorothioates are proposed as novel analogues of myo-inositol phosphates; their resistance to phosphatase-catalysed breakdown is reported.
Hamblin
M R
MR
Department of Chemistry, Leicester University, U.K.
Flora
J S
JS
Potter
B V
BV
D000469:Alkaline Phosphatase; D007295:Inositol Phosphates / Q000138:chemical synthesis*; D008956:Models, Chemical; D013403:Sugar Phosphates / Q000138:chemical synthesis*
D007295:Inositol Phosphates; D013403:Sugar Phosphates; C054233:inositol 1,4-bisphosphorothioate; C044259:inositol 1,4-bis(phosphate); D000469:Alkaline Phosphatase