BENZOPHENONE PHOTOPHORES IN BIOCHEMISTRY
BENZOPHENONE PHOTOPHORES IN BIOCHEMISTRY
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DOI：
10.1021/bi00185a001
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发表时间：
1994-05-17
期刊：
影响因子：
2.9
通讯作者：
PRESTWICH, GD
中科院分区：
文献类型：
--
作者：
DORMAN, G;PRESTWICH, GD
近5年来，可光活化的芳基酮类化合物作为生化探针被重新发现。二苯甲酮(BP)光探针的广泛应用可以归因于三个明显的化学和生物化学优势。首先，对苯二酚在化学上比重氮酸酯、芳基叠氮化合物和二氮杂环化合物更稳定。其次，BPS可以在环境光中操纵，并可以在350-360 nm处激活，避免了对蛋白质造成破坏的波长。第三，BPS优先与未反应的C-H键反应，即使在溶剂水和大量亲核试剂存在的情况下也是如此。这三种性质结合在一起，产生了高效率的大分子共价修饰，通常具有显著的位点特异性。这一视角包括对BP光化学的简要回顾和这些光探针的特定应用的选择，这些光探针解决蛋白质、核酸和脂肪生物化学中的问题。
The photoactivatable aryl ketone derivatives have been rediscovered as biochemical probes in the last 5 years. The expanding use of benzophenone (BP) photoprobes can be attributed to three distinct chemical and biochemical advantages. First, BPs are chemically more stable than diazo esters, aryl azides, and diazirines. Second, BPs can be manipulated in ambient light and can be activated at 350-360 nm, avoiding protein-damaging wavelengths. Third, BPs react preferentially with unreactive C-H bonds, even in the presence of solvent water and bulk nucleophiles. These three properties combine to produce highly efficient covalent modifications of macromolecules, frequently with remarkable site specificity. This Perspective includes a brief review of BP photochemistry and a selection of specific applications of these photoprobes, which address questions in protein, nucleic acid, and lipid biochemistry.