Cell surface engineering by a modified Staudinger reaction
Cell surface engineering by a modified Staudinger reaction
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DOI：
10.1126/science.287.5460.2007
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发表时间：
2000-03-17
期刊：
影响因子：
56.9
通讯作者：
Bertozzi, CR
中科院分区：
文献类型：
--
作者：
Saxon, E;Bertozzi, CR
在细胞环境中发生的选择性化学反应可以是阐明生物过程或工程设计新相互作用的有力工具。一种化学转化，允许选择性地形成共价加合物之间的丰富功能化的生物聚合物在细胞内的上下文。在施陶丁格反应之后建模的连接通过叠氮化物和特定工程化的三芳基膦的偶联形成酰胺键。这两种反应伴侣都是非生物的，并且与天然细胞组分化学正交。通过合成叠氮糖的代谢安装在细胞表面糖缀合物内的叠氮化物与生物素化的三芳基膦反应以产生稳定的细胞表面加合物。这种转化的巨大选择性应该允许它在细胞内部执行，为探测细胞内相互作用提供了新的可能性。
Selective chemical reactions enacted within a cellular environment can be powerful tools for elucidating biological processes or engineering novel interactions. A chemical transformation that permits the selective formation of covalent adducts among richly functionalized biopolymers within a cellular context is presented. A ligation modeled after the Staudinger reaction forms an amide bond by coupling of an azide and a specifically engineered triarylphosphine. Both reactive partners are abiotic and chemically orthogonal to native cellular components. Azides installed within cell surface glycoconjugates by metabolism of a synthetic azidosugar were reacted with a biotinylated triarylphosphine to produce stable cell-surface adducts. The tremendous selectivity of the transformation should permit its execution within a cell's interior, offering new possibilities for probing intracellular interactions.