Fmoc-SPPS chemistry compatible approach for the generation of (glyco)peptide aryl thioesters |
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Authors: | Ji-Shen Zheng Wei-Xian XiFeng-Liang Wang Juan Li Qing-Xiang Guo |
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Institution: | a Department of Chemistry, University of Science and Technology of China, Hefei 230026, China b Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China |
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Abstract: | A new approach is described for the general Fmoc-based solid-phase synthesis of (glyco)peptide aryl thioesters. A peptide alkyl oxoester obtained by standard Fmoc-based chain elongation undergoes an O-to-S acyl shift, and is followed by alkyl thioester exchanges with a large excess of aryl thiol, affording the corresponding peptide aryl thioester. The newly developed methodology is useful for the chemical synthesis of post-translationally modified proteins because of its compatibility with standard Fmoc-SPPS conditions. In addition, the peptide aryl thioesters are essential intermediates for chemical synthesis of proteins by kinetically controlled convergent strategy. |
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