Synthesis of a fluorescent photoaffinity probe of OSW-1 by site-selective acylation of an inactive congener and biological evaluation
Synthesis of a fluorescent photoaffinity probe of OSW-1 by site-selective acylation of an inactive congener and biological evaluation
复制标题
通过非活性同系物的位点选择性酰化合成 OSW-1 荧光光亲和探针并进行生物学评价
DOI：
10.1016/j.bmcl.2016.08.053
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发表时间：
2017
影响因子：
4.9
通讯作者：
Y.
中科院分区：
文献类型：
--
作者：
Sakurai;K.;Hiraizumi;M., Isogai;N.;Komatsu;R.;Shibata;T.;Ohta;Y.
细胞表面的糖脂-蛋白相互作用涉及多种生物过程。为了研究糖脂结合蛋白，我们设计并合成了三功能光亲和探针，该探针将糖头基团与含有光反应基团和荧光标记的脂尾单元结合。对含二苯甲酮基团和重氮嘧啶基团的糖脂光亲和探针对碳水化合物头基团特异性蛋白的光交联反应性进行了评价。在涉及竞争配体的比较分析中，发现基于重氮嘧啶的糖脂光亲和探针比基于二苯甲酮的探针更有效地区分特定的结合蛋白。
Glycolipid–protein interactions at the cell surface are implicated in various biological processes. Toward the investigation of glycolipid binding proteins, we designed and synthesized trifunctional photoaffinity probes, which present a sugar head group with a triazole linkage to the lipid tail unit containing a photoreactive group and a fluorescent tag. The glycolipid photoaffinity probes bearing benzophenone group or diazirine group were evaluated for their photocrosslinking reactivity toward a carbohydrate head group specific protein. The diazirine based glycolipid photoaffinity probe was found to be more effective than the benzophenone-based probe in a comparative analysis involving a competitive ligand to distinguish a specific binding protein.