Hmboff/on as a switchable thiol protecting group for native chemical ligation

Yun-Kun Qi; Shan Tang; Yi-Chao Huang; Man Pan; Ji-Shen Zheng; Lei Liu

doi:10.1039/C6OB00450D

Hmb^off/on as a switchable thiol protecting group for native chemical ligation

Yun-Kun Qi,^a^b Shan Tang,^a Yi-Chao Huang,^a Man Pan,^a Ji-Shen Zheng*^b and Lei Liu*^a

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* Corresponding authors

^a 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
E-mail: lliu@mail.tsinghua.edu.cn

^b High Magnetic Field Laboratory, Chinese Academy of Sciences, Hefei 230031, China
E-mail: jszheng@hmfl.cas.cn

Abstract

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[Cys⁹⁸–Arg¹⁶⁶]-OH through native chemical ligation.

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Publication details

The article was received on 27 Feb 2016, accepted on 14 Apr 2016 and first published on 14 Apr 2016

Article type: Communication

DOI: 10.1039/C6OB00450D

Citation: Org. Biomol. Chem., 2016,14, 4194-4198

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Hmb^off/on as a switchable thiol protecting group for native chemical ligation

Y. Qi, S. Tang, Y. Huang, M. Pan, J. Zheng and L. Liu, Org. Biomol. Chem., 2016, 14, 4194
DOI: 10.1039/C6OB00450D
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Organic & Biomolecular Chemistry

Hmb^off/on as a switchable thiol protecting group for native chemical ligation

Abstract

Supplementary files

Publication details

Hmb^off/on as a switchable thiol protecting group for native chemical ligation

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