Citation: Min Fu, Pan He, Sen Zhou, Wenqiang Liu, Bo Ma, Shiying Shang, Yaohao Li, Ruihan Wang, Zhongping Tan. An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation[J]. Chinese Chemical Letters, ;2024, 35(8): 109434. doi: 10.1016/j.cclet.2023.109434 shu

An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation

Min Fu ^a ,
Pan He ^a ,
Sen Zhou ^a ,
Wenqiang Liu ^a ,
Bo Ma ^a ,
Shiying Shang ^b ,
Yaohao Li ^{a, *,} ,
Ruihan Wang ^{a, c, *,} ,
Zhongping Tan ^{a, *,}

a.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
Center of Pharmaceutical Technology, School of Pharmaceutical Sciences, Tsinghua University, Beijing 100084, China
c.
Chemical Engineering College, Hebei Normal University of Science and Technology, Qinhuangdao 066600, China

yaohaoli@imm.ac.cn

ruihanwang@imm.ac.cn

zhongping.tan@imm.ac.cn

Received Date: 15 October 2023
Revised Date: 2 December 2023
Accepted Date: 11 December 2023
Available Online: 21 December 2023

Figures(6)

This study presents an unexpected finding that the cis isomer of β-thio-Asp exhibits higher ligation activity than the trans isomer. This discovery sheds light on the intricate nature of native chemical ligation and highlights the importance of factors beyond the steric effects of the side chain in modulating ligation activity.
- Native chemical ligation,
- Stereochemistry,
- Ligation activity,
- β-Thio-Asp,
- Intramolecular hydrogen bond
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