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作为了解选择性的关键,对不对称器官催化物的分子间相互作用进行量化

Jens Nowag¹, Matthias Brauser¹, Lisa Steuernagel¹

¹Clemens-Schöpf-Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Peter-Grünberg-Straße 16, D-64287 Darmstadt, Germany.

Journal of the American Chemical Society

|December 20, 2023

概括

一种脂性寡催化剂在溶解转环-1,2-二醇方面表现出高的选择性. 核磁共振 (NMR) 光谱量化相互作用能量,揭示分子识别有利于 (R,R) 变异体.

科学领域:

有机化学
生物催化
光谱学

背景情况:

使用脂性寡催化剂的转环-1,2-二醇的动态分辨率.
在之前的研究中观察到的异常选择性.

研究的目的:

阐明控制催化剂选择性的因素.
量化催化剂和二醇反体之间相互作用的吉布斯自由能量.

主要方法:

核磁共振 (NMR) 光谱,包括横向放松 (R2),扩散测量,和转移差异 (STD) 和化学转移 (δ) 分析.
用于分析二醇混合物的NMR定位.
化阶段的反应监测.

主要成果:

通过各种先进的NMR技术获得的可比且一致的结果.
分子识别量化为大约3kJmol-1有利于 (R,R) -enantiomer.
通过催化化反应监测证实了相互作用能量差异.

结论:

脂友性寡催化剂对转环-1,2-二醇的 (R,R) - 反体具有显著的选择性.
在中催化剂和基质的自我结合在选择性中起着至关重要的作用.
了解自我关联对于优化反应选和催化剂设计至关重要.

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