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Synthesis of Multi Amino Acid Chiral Polymeric Microparticles for Enantioselective Chemistry
Macromolecular Chemistry and Physics ( IF 2.5 ) Pub Date : 2020-11-23 , DOI: 10.1002/macp.202000328
Meir Abuaf 1 , Yitzhak Mastai 1
Affiliation  

Chiral polymeric particles have emerged as a new and exciting field of research and in the last years due to their possible use for many applications in chiral chemistry. In this article, an important question is focused upon that has not been explored in detail in the field of chiral polymeric particles. The main question is whether the chiral composition of the polymeric particles affects their chiral recognition. The hypothesis is that chiral polymeric particles with a variety of different chiral groups will improve chiral recognition and improve their use of enantioselectivity crystallization. Consequently, chiral microparticles based on one up to three different amino acids based monomers are prepared by precipitation polymerization. The chiral microspheres are characterized by dynamic light scattering, scanning electron microscope (SEM), mass spectrometry (MS), and nuclear magnetic resonance (NMR) and display a narrow size distribution in the range of 1–2 μm. The chiral discrimination ability of these chiral microspheres for enantioselective crystallization is studied in the crystallization of DL‐leucine crystallization, as a model system. Time‐resolved polarimetry, X‐ray diffraction (XRD), and differential scanning calorimetry (DSC) are used to provide evidence for enantioselective crystallization. Surprisingly the results show that only particles composed of one amino acids monomers show the best results for enantioselective crystallization.

中文翻译:

对映选择性化学的多氨基酸手性聚合物微粒的合成

手性聚合物颗粒已经成为新的令人兴奋的研究领域,并且由于它们可能在手性化学中的许多应用而在最近几年出现。在本文中,一个重要的问题集中在手性聚合物颗粒领域中尚未详细探讨的问题上。主要问题是聚合物颗粒的手性组成是否会影响其手性识别。该假设是具有多种不同手性基团的手性聚合物颗粒将改善手性识别能力,并改善其对映选择性结晶的使用。因此,通过沉淀聚合制备了基于一种至多三种基于氨基酸的单体的手性微粒。手性微球的特征在于动态光散射,扫描电子显微镜(SEM),质谱(MS)和核磁共振(NMR),并且在1-2μm的范围内显示出狭窄的尺寸分布。作为模型系统,在DL-亮氨酸结晶过程中研究了这些手性微球对映体选择性结晶的手性鉴别能力。时间分辨极化仪,X射线衍射(XRD)和差示扫描量热法(DSC)用于提供对映选择性结晶的证据。令人惊讶地,结果表明,仅由一种氨基酸单体组成的颗粒显示出对映选择性结晶的最佳结果。作为模型系统,在DL-亮氨酸结晶中研究了这些手性微球对映选择性结晶的手性鉴别能力。时间分辨极化仪,X射线衍射(XRD)和差示扫描量热法(DSC)用于提供对映选择性结晶的证据。令人惊讶地,结果表明,仅由一种氨基酸单体组成的颗粒显示出对映选择性结晶的最佳结果。作为模型系统,在DL-亮氨酸结晶过程中研究了这些手性微球对映体选择性结晶的手性鉴别能力。时间分辨极化仪,X射线衍射(XRD)和差示扫描量热法(DSC)用于提供对映选择性结晶的证据。令人惊讶地,结果表明,仅由一种氨基酸单体组成的颗粒显示出对映选择性结晶的最佳结果。
更新日期:2020-12-18
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