128(P80) イノシトールリン脂質類の合成(ポスター発表の部)
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概要
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Recently, inositol phospholipids located within the plasma membrane have received much attention due to their biological interests in the intracellular signal transduction system. In order to achieve their efficient chemical synthesis, new synthetic methodologies were required. From this standpoint, we have investigated a regioselective phosphorylation and glycosylation methodologies based on the phosphite chemistry. We also developed a new protecting group (PAC) for a hydroxyl group. These methods were demonstrated to be effective for the synthesis of inositol phospholipids. Synthetic methodologies aiming at inositol phospholipid synthesis Regioselective phosphorylation methodology Treatment of trimethyl and tribenzyl phosphites with pyridinium tribromide in the presence of an alcohol and a tert-amine furnished the phosphoric triesters in high yields (Scheme 1). This method was found to be effectively applicable to regioselective phosphorylation of 1,2-free inositol derivatives giving 1-O-phosphate as shown in the schemes. Glycosylation using glycosyl phosphites A glycosyl phosphite was found to react with an alcohol in the presence of Lewis acid such as ZnCl_2-AgClO_4 and NIS-TfOH giving the glycoside in good yield (Scheme 1). The method can be shown to be widely applicable. A new protecting group As a new protecting group which plays a role in a kinetic resolution of an inositol derivative as well as protection of a hydroxyl function, the 2-(2-O-substituted-ethyl)benzoyl group was found to be ideal (Scheme 2). Synthesis of phosphatidylinositol derivatives Using the new methods described above, phosphatidylinositol 3,4,5-trisphosphate (Scheme 3) and 2,6-di-O-mannopyranosyl-1-phosphatidyl-myo-inositol (Scheme 4) were efficiently prepared.
- 天然有機化合物討論会の論文
- 1996-09-02
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