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在伪稀释条件下通过利用布朗斯特德酸激活N-Chlorosuccinimide在酸中引入区域选择性二硫化物链接

Nitesh Mani Tripathi¹, Basab Kanti Das¹, Arnab Chowdhury¹

¹Biomimetic Peptide Engineering Laboratory, Department of Chemistry, Indian Institute of Technology, Ropar, Rupnagar, Punjab140001, India.

|February 28, 2025

概括

一种新的在树脂上的方法简化了酸中二硫化键的形成,使用广泛可用的氨酸保护组和酸激活的N-chloro-succinimide. 这种高效的方法可以快速合成复杂的富含二硫化物.

科学领域:

类化学类化学
有机合成有机合成
生物技术是生物技术.

背景情况:

富含二硫化物的固体相合成至关重要,但往往需要复杂的正交化学和专门的构建块.
现有的在树脂二硫化物组装方法可能涉及多个步骤来保护组去除,限制效率.

研究的目的:

开发一种新的,操作简单的,高效的在树脂上的方法,用于组装多个二硫化物键.
引入一种新的正交构建块,用于使用可访问的氨酸保护组进行单步二硫化物形成.

主要方法:

使用酸激活的N-糖胺 (NCS) 与常见的囊蛋白保护组 (Trt,Acm,tBu) 用于在树脂上的二硫化物组装.
研究了2%三酸 (TFA) 激活的NCS对快速和清洁的二硫化物形成的有效性.
整合了TFA-NCS方法与先前建立的I2/S2O8(2-) 介导的协议,用于顺序的二硫化物键形成.

主要成果:

S-tBu 氨酸成为单步二硫化物组装的有效直角构建块.
2% TFA 激活的 NCS 快速 (∼15 分钟) 在各种序列中产生清洁的二硫化物产物.
综合策略使得在约30分钟内能够在毒素,素和新中形成两个二硫化键的区域选择性形成.
密度功能理论 (DFT) 的计算支持了NCS激活机制,促进了二硫化物组装.

结论:

开发的TFA-NCS方法为在树脂上的二硫化物组装提供了一种高生产率和操作简单的方法.
这种方法通过利用可访问的保护组和减少反应步骤来简化富含二硫化物的合成.
该策略在新二硫化物合成中具有广泛应用的巨大潜力.

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