Peptide o‐Aminoanilides as Crypto‐Thioesters for Protein Chemical Synthesis |
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| Authors: | Yao He Da‐Liang Qu Min Yu Prof. Zhang‐Yong Hong Prof. Dr. Lei Liu |
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| Affiliation: | 1. School of Life Sciences, University of Science and Technology of China, Hefei 230026 (China);2. State Key Laboratory of Medicinal Chemical Biology, College of Life Sciences, Nankai University, Tianjin 300071 (China);3. Tsinghua‐Peking Center for Life Sciences, Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China) |
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| Abstract: | Fully unprotected peptide o‐aminoanilides can be efficiently activated by NaNO2 in aqueous solution to furnish peptide thioesters for use in native chemical ligation. This finding enables the convergent synthesis of proteins from readily synthesizable peptide o‐aminoanilides as a new type of crypto‐thioesters. The practicality of this approach is shown by the synthesis of histone H2B from five peptide segments. Purification or solubilization tags, which are sometimes needed to improve the efficiency of protein chemical synthesis, can be incorporated into the o‐aminoanilide moiety, as demonstrated in the preparation of the cyclic protein lactocyclicin Q. |
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| Keywords: | native chemical ligation peptide o‐aminoanilides peptide thioesters proteins sodium nitrite |
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