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| Glycopeptide ligation via direct aminolysis of selenoester |
| Jing-Jing Dua, Ling-Ming Xina, Ze Leia, Shi-Yao Zoua, Wen-Bo Xua, Chang-Wei Wanga, Lian Zhanga, Xiao-Fei Gaoa,b, Jun Guoa |
a Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, College of Chemistry, Central China Normal University, Wuhan 430079, China;
b Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation, East China University of Technology, Nanchang 330013, China |
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| Guide In this work, the selenoester of unprotected glycopeptide was readily prepared, and the direct aminolysis of glycopeptide selenoester was successfully applied to synthesize MUC1 mucin sequence. |
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Abstract Direct aminolysis of selenoester in aqueous media was investigated as a glycopeptide ligation strategy. This strategy allows the peptide and glycopeptide ligation to proceed smoothly (even with hindered amino acids) without the need of cysteine residue, N-terminal thiol auxiliary or coupling additive, and to afford the corresponding amide products in excellent yields. No epimerization was observed during ligation reations. In this work, the selenoester of unprotected glycopeptide was readily prepared, and the direct aminolysis of glycopeptide selenoester was successfully applied to synthesize MUC1 mucin sequence efficiently.
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Received: 20 March 2018
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| Fund:This work is supported by the National Key Research and Development Program of China (No. 2017YFA0505200), the National Natural Science Foundation of China (No. 21772056), Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation Open Foundation (No. JXMS201701), the self-determined research funds of CCNU from the colleges' basic research and operation of MOE (No. CCNU18TS011) and the Program of Introducing Talents of Discipline to Universities of China (111 program, No. B17019). |
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Corresponding Authors:
Xiao-Fei Gao, sandy2005327@126.com;Jun Guo, jguo@mail.ccnu.edu.cn, 1514910982@qq.com
E-mail: sandy2005327@126.com;jguo@mail.ccnu.edu.cn,1514910982@qq.com
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