Citation: Du Jing-Jing, Xin Ling-Ming, Lei Ze, Zou Shi-Yao, Xu Wen-Bo, Wang Chang-Wei, Zhang Lian, Gao Xiao-Fei, Guo Jun. Glycopeptide ligation via direct aminolysis of selenoester[J]. Chinese Chemical Letters, ;2018, 29(7): 1127-1130. doi: 10.1016/j.cclet.2018.04.016 shu

Glycopeptide ligation via direct aminolysis of selenoester

Du Jing-Jing ^a,1 ,
Xin Ling-Ming ^a,1 ,
Lei Ze ^a ,
Zou Shi-Yao ^a ,
Xu Wen-Bo ^a ,
Wang Chang-Wei ^a ,
Zhang Lian ^a ,
Gao Xiao-Fei ^a,b,, ,
Guo Jun ^a,,

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

Corresponding author: Gao Xiao-Fei, sandy2005327@126.com Guo Jun, jguo@mail.ccnu.edu.cn; 1514910982@qq.com

Received Date: 20 March 2018
Revised Date: 3 April 2018
Accepted Date: 13 April 2018
Available Online: 18 July 2018

Figures(3)

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.
- Glycolpeptide,
- Aminolysis,
- Selenoester,
- Additive-free,
- MUC1 mucin
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