盐化酒石酸衍生物手性拆分dl-亮氨酸

IF 2.6 3区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
CrystEngComm Pub Date : 2024-12-10 DOI:10.1039/D4CE01043D
Linlin Shi, Zhiqiang Guo, Xiaofang Luo, Lingli Hou, Hongchang Wu, Ruiyu De, Xin Huang, Ting Wang, Hongxun Hao, Na Wang and Lina Zhou
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引用次数: 0

摘要

非对映体盐的形成适合于外消旋化合物的手性拆分,是获得对映体的最有效方法。目前,dl -亮氨酸(DL-LEU)的分离方法较少,其分离机理也未进行研究。本研究选择(+)-二-1,4-甲苯-d -酒石酸一水合物(D-DTTA)作为配体。采用液体辅助研磨法合成了非对映体盐D-LEU:D-DTTA (D-D)和L-LEU:D-DTTA (L-D),并用粉末x射线衍射、热分析、傅里叶变换红外光谱和单晶x射线衍射对其进行了鉴定。它们在晶体结构、热力学性质和分子间相互作用方面的差异表明,D-D更稳定,溶解度更低,这使得手性拆分成为可能。此外,对D-DTTA的手性识别机制进行了研究,发现D-DTTA更容易与D-LEU结合。最后确定了最佳的分离条件,通过多段结晶工艺,D-D和L-D的ee值分别达到91.20%和- 73.32%。本研究为DL-LEU外消旋化合物的分离提供了一种有效且工业适用的方法,并为成盐性手性拆分剂的筛选提供了参考。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Chiral resolution of dl-leucine via salifying tartaric acid derivatives†

Chiral resolution of dl-leucine via salifying tartaric acid derivatives†

Diastereomeric salt formation is suitable for chiral resolution of racemic compounds and is the most effective way to obtain enantiomers. At present, there are few resolution methods for DL-leucine (DL-LEU), and the corresponding mechanism of resolution has not been studied. In this study, (+)-di-1,4-toluoyl-D-tartaric acid monohydrate (D-DTTA) was selected as the ligand. Diastereomeric salts D-LEU:D-DTTA (DD) and L-LEU:D-DTTA (LD) were synthesized by liquid-assisted grinding and then identified by powder X-ray diffraction, thermal analysis, Fourier transform infrared spectroscopy and single crystal X-ray diffraction. Their difference in crystal structures, thermodynamic properties and intermolecular interactions showed that DD is more stable and has lower solubility, which makes chiral resolution possible. Furthermore, the mechanism of chiral recognition was investigated, which showed that D-DTTA was more easily bound to D-LEU. Finally, the optimized resolution condition was confirmed, and the ee values of DD and LD reached 91.20% and −73.32% respectively by the multi-stage crystallization process. This study provides an effective and industrially applicable method for the separation of the DL-LEU racemic compound, and provides a reference for the screening of salt-forming chiral resolution agents.

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来源期刊
CrystEngComm
CrystEngComm 化学-化学综合
CiteScore
5.50
自引率
9.70%
发文量
747
审稿时长
1.7 months
期刊介绍: Design and understanding of solid-state and crystalline materials
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