Hamblin M R, Flora J S, Potter B V
Department of Chemistry, Leicester University, U.K.
Biochem J. 1987 Sep 15;246(3):771-4. doi: 10.1042/bj2460771.
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.
报道了通过对(±)-1,2:4,5-二异亚丙基-myo-肌醇使用亚磷酸酯化学方法合成第二信使肌醇1,4,5-三磷酸的代谢产物肌醇1,4-二磷酸及其类似物1,4-二硫代磷酸酯。(±)-1,2:4,5-二异亚丙基3,6-双[二(2-氰基乙基)]亚磷酸酯的合成提供了一种中间体,该中间体可被氧化为相应的二磷酸酯或二硫代磷酸酯。肌醇硫代磷酸酯被认为是肌醇磷酸酯的新型类似物;报道了它们对磷酸酶催化分解的抗性。