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Enantioselective Crystallization on Chiral Polymeric Microspheres

机译:手性聚合物微球上的对映选择性结晶

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摘要

In this article, a new approach to chiral resolution based on enantioselective crystallization on chiral polymeric microspheres is presented. To demonstrate the approach, a new synthetic method is developed for the preparation of porous and hollow chiral polymeric microspheres. Chiral microspheres based on poly(N-vinyl α-L-phenylalanine) (PV-L-Phe) are synthesized from uniform polystyrene (PS) microsphere templates by a single-step swelling process. The chiral microspheres display a narrow size distribution, and their properties, especially the porosity, can be controlled by varying the synthesis conditions. The chiral discrimination ability of these chiral microspheres is studied for DL-valine crystallization, as a model system for chiral racemic crystallization. X-ray diffraction (XRD) and differential scanning calorimetry (DSC) provide evidence for the crystallization of enantiopure crystals on the chiral polymeric microspheres. Optical rotation measurements during crystallization show an ena-tiomeric excess of ca. 25 % for L-valine in the chiral microspheres. Although this excess is not yet very high, the basic principle of chiral discrimination by enantioselective crystallization on chiral microspheres is demonstrated.
机译:在本文中,提出了一种基于手性聚合物微球上对映选择性结晶的手性拆分新方法。为了证明该方法,开发了一种用于制备多孔和中空手性聚合物微球的新合成方法。基于聚(N-乙烯基α-L-苯丙氨酸)(PV-L-Phe)的手性微球是通过均匀的聚苯乙烯(PS)微球模板通过一步溶胀过程合成的。手性微球的粒径分布窄,可以通过改变合成条件来控制其性质,尤其是孔隙率。作为手性外消旋结晶的模型系统,研究了这些手性微球的手性鉴别能力对DL-缬氨酸的结晶。 X射线衍射(XRD)和差示扫描量热法(DSC)为手性聚合物微球上对映纯晶体的结晶提供了证据。结晶过程中的旋光度测量显示约有对映体过量。 L-缬氨酸在手性微球中占25%。尽管这种过量还不是很高,但是通过手性微球上对映选择性结晶的手性鉴别的基本原理得到了证明。

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