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Electrostatic Assistance of 4-Mercaptophenylacetic acid catalyzed Native Chemical Ligation
ChemRxiv Pub Date : 2023-03-10 , DOI: 10.26434/chemrxiv-2023-1k49m
Nathalie Ollivier 1 , Eliott Roy 1 , Rémi Desmet 1 , Vangelis Agouridas 2 , Vincent Diemer 3 , Oleg Melnyk 1, 3, 4, 5
Affiliation  

4-mercaptophenylacetic acid (MPAA) is a popular catalyst of the native chemical ligation (NCL) but has to be used in large excess for achieving practically useful rates (up to 50-100 equivalents). We report here that the catalytic potency of MPAA can be boosted by introducing a stretch of arginines in the departing thiol from the thioester. By doing so, the electrostatically-assisted NCL reaction proceeded rapidly by using sub-stoichiometric concentrations of MPAA, an advantage that enabled useful synthetic applications.

中文翻译:

4-巯基苯乙酸催化天然化学连接的静电辅助

4-巯基苯乙酸 (MPAA) 是天然化学连接 (NCL) 的常用催化剂,但必须大量使用才能达到实际有用的速率(高达 50-100 当量)。我们在此报告,通过在硫酯的离去硫醇中引入一段精氨酸,可以提高 MPAA 的催化效力。通过这样做,静电辅助的 NCL 反应通过使用亚化学计量浓度的 MPAA 快速进行,这一优势使得有用的合成应用成为可能。
更新日期:2023-03-10
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