Qi Yun-Kun, Tang Shan, Huang Yi-Chao, Pan Man, Zheng Ji-Shen, Liu Lei
Tsinghua-Peking Center for Life Sciences, Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China.
High Magnetic Field Laboratory, Chinese Academy of Sciences, Hefei 230031, China.
Org Biomol Chem. 2016 May 4;14(18):4194-8. doi: 10.1039/c6ob00450d.
A new thiol protecting group Hmb(off/on) is described, which has a switchable activity that may be useful in the chemical synthesis of proteins. When placed on the side chain of Cys, Cys(Hmb(off)) is stable to trifluoroacetic acid (TFA) in the process of solid-phase peptide synthesis. When Cys(Hmb(off)) is treated with neutral aqueous buffers, it is cleanly converted to acid-labile Cys(Hmb(on)), which can later be fully deprotected by TFA to generate free Cys. The utility of Cys(Hmb(off/on)) is demonstrated by the chemical synthesis of an erythropoietin segment, EPO[Cys(98)-Arg(166)]-OH through native chemical ligation.
描述了一种新的硫醇保护基Hmb(off/on)，其具有可切换的活性，这在蛋白质的化学合成中可能有用。当连接到半胱氨酸（Cys）的侧链上时，Cys(Hmb(off))在固相肽合成过程中对三氟乙酸（TFA）稳定。当用中性水性缓冲液处理Cys(Hmb(off))时，它会干净地转化为对酸不稳定的Cys(Hmb(on))，随后可以用TFA完全脱保护以生成游离的半胱氨酸。通过天然化学连接法合成促红细胞生成素片段EPO[Cys(98)-Arg(166)]-OH，证明了Cys(Hmb(off/on))的实用性。
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