Synthesis of photoactivatable 1,2-O-diacyl-sn-glycerol derivatives of 1-L-phosphatidyl-D-myo-inositol 4,5-bisphosphate (PtdInsP(2)) and 3,4,5-trisphosphate (PtdInsP(3))
Synthesis of photoactivatable 1,2-O-diacyl-sn-glycerol derivatives of 1-L-phosphatidyl-D-myo-inositol 4,5-bisphosphate (PtdInsP(2)) and 3,4,5-trisphosphate (PtdInsP(3))
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DOI：
10.1021/jo960895r
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发表时间：
1996-09-06
影响因子：
3.6
通讯作者：
Prestwich, GD
中科院分区：
文献类型：
--
作者：
Chen, J;Profit, AA;Prestwich, GD
1-L-磷脂酰-D-肌醇 4,5-二磷酸 (PtdIns(4,5)P-2 或 PtdInsP(2)) 和相应的 3,4,5-三磷酸 (PtdIns(3,4,5)P-3 或 PtdInsP(3)) 的光活化类似物是由两种手性前体甲基制备的。 a-D-吡喃葡萄糖苷和1,2-异丙叉-sn-甘油。两个关键的合成转化包括构建光学纯肌醇骨架的费里尔重排反应以及甘油衍生物上伯羟基和仲羟基的顺序酰化。 sn-1-O-(6-氨基己酰基) PtdInsP(2) 和 PtdInsP(3) 衍生物经过进一步修饰，以包含未标记和高比活性氚标记形式的二苯甲酮发光团。
Photoactivatable analogues of 1-L-phosphatidyl-D-myo-inositol 4,5-bisphosphate (PtdIns(4,5)P-2 or PtdInsP(2)) and the corresponding 3,4,5-trisphosphate (PtdIns(3,4,5)P-3 or PtdInsP(3)) were prepared from the two chiral precursors, methyl a-D-glucopyranoside and 1,2-isopropylidene-sn-glycerol. Two key synthetic transformations included the Ferrier rearrangement reaction to construct the optically-pure inositol skeleton and the sequential acylation of the primary and secondary hydroxyl groups on the glycerol derivatives. The sn-1-O-(6-aminohexanoyl) PtdInsP(2) and PtdInsP(3) derivatives were further modified to contain benzophenone photophores in unlabeled and high specific activity tritium-labeled forms.