Fujita Yuji, Murakami Yoshihiro, Noda Akihiro, Miyoshi Sosuke
Drug Discovery Research, Astellas Pharma Inc. , Tsukuba 305-8585, Japan.
Bioconjug Chem. 2017 Feb 15;28(2):642-648. doi: 10.1021/acs.bioconjchem.6b00707. Epub 2017 Jan 13.
An easily obtainable thiol-selective labeling reagent [F]FBSEM (N-[2-(4-[F]fluoro-N-methylbenzenesulfonamido)ethyl]maleimide) was developed. The advantage of the design is that the precursor and [F]FBSEM have the same backbone and backbone construction is not required; in contrast, known thiol-specific labeling reagents do require backbone construction, and this is thought to be the cause of their complicated synthesis. [F]FBSEM was successfully obtained in higher yield (25%) and in a simpler way (two fluorination and deprotection steps in 65 min) than the widely used [F]FBEM (N-[2-(4-[F]fluorobenzamide)ethyl]maleimide). The labeling efficacy of [F]FBSEM was confirmed by conjugation with glutathione. [F]FBSEM is a promising labeling agent for proteins.
开发了一种易于获得的硫醇选择性标记试剂[F]FBSEM（N-[2-(4-[F]氟-N-甲基苯磺酰胺基)乙基]马来酰亚胺）。该设计的优点在于前体和[F]FBSEM具有相同的主链，无需构建主链；相比之下，已知的硫醇特异性标记试剂确实需要构建主链，这被认为是其合成复杂的原因。与广泛使用的[F]FBEM（N-[2-(4-[F]氟苯甲酰胺)乙基]马来酰亚胺）相比，[F]FBSEM以更高的产率（25%）和更简单的方式（在65分钟内进行两步氟化和脱保护步骤）成功获得。通过与谷胱甘肽偶联证实了[F]FBSEM的标记效果。[F]FBSEM是一种很有前景的蛋白质标记剂。
