Synthesis and properties of photoactivatable phospholipid derivatives designed to probe the membrane-associate domains of proteins
Synthesis and properties of photoactivatable phospholipid derivatives designed to probe the membrane-associate domains of proteins
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DOI：
10.1021/jo951350k
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发表时间：
1996-01-12
影响因子：
3.6
通讯作者：
Goeldner, M
中科院分区：
文献类型：
--
作者：
Alcaraz, ML;Peng, L;Goeldner, M
描述了可光活化的磷脂探针1和2的全合成。这些探针在其极性头部含有芳基重氮功能（探针Ia和Ib）或连接到一个脂肪酸侧链末端的重氮环己二烯酮基（探针2），并且已经被设计为分别探测膜的脂质/水界面和疏水核心。合成方案包括纳入放射性标记的原子（氚）的可能性，用于进一步的标记调查。这两种探针在生理条件下在黑暗中是稳定的，并可以有效地在300 nm以上的波长光解，导致产生高活性的物种，芳基阳离子和环己二烯基卡宾，分别。此外，这些探针显示的UV吸收光谱与Dahan介导的能量转移光活化相容，这可能导致膜相关蛋白结构域的有效映射。
The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes la and Ib) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.