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.

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.
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肌醇硫代磷酸酯,肌醇磷酸酯的磷酸酶抗性类似物。

DOI:
10.1042/bj2460771
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发表时间:
1987
期刊:
The Biochemical journal
影响因子:
--
通讯作者:
B. Potter
B. Potter
中科院分区:
--
文献类型:
--
作者:
Michael R Hamblin;J. S. Flora;B. Potter

文献摘要

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本文报道了用亚磷酸盐化学法合成第二信使肌醇1,4,5-三磷酸盐的代谢产物肌醇1,4-二磷酸盐及其类似物1,4-二硫代磷酸盐。(+/-)-1,2:4,5-二异亚丙基3,6-双[二-(2-氰乙基)]亚磷酸酯的合成提供了一种中间体,其可以被氧化为相应的二磷酸酯或二硫代磷酸酯。肌醇硫代磷酸酯被提出作为肌醇磷酸酯的新类似物;报道了它们对磷酸酶催化的分解的抗性。
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.