An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation
Min Fu 1Pan He 1Sen Zhou 1Wenqiang Liu 1Bo Ma 1Shiying Shang 2Yaohao Li 1Ruihan Wang 3Zhongping Tan1
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作者信息
1. State Key Laboratory of Bioactive Sub stance and Function of Natural Medicines,Institute of Materia Medica,Chinese Academy of Medical Sciences and Peking Union Medical College,Beijing 100050,China
2. Center of Pharmaceutical Technology,School of Pharmaceutical Sciences,Tsinghua University,Beijing 100084,China
3. 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;Chemical Engineering College,Hebei Normal University of Science and Technology,Qinhuangdao 066600,China
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Abstract
This study presents an unexpected finding that the cis isomer of β-thio-Asp exhibits higher ligation ac-tivity 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.
Key words
Native chemical ligation/Stereochemistry/Ligation activity/β-Thio-Asp/Intramolecular hydrogen bond
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