Synthesis of Multi Amino Acid Chiral Polymeric Microparticles for Enantioselective Chemistry

Meir Abuaf, Yitzhak Mastai

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

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.

Original languageEnglish
Article number2000328
JournalMacromolecular Chemistry and Physics
Volume221
Issue number24
Early online date23 Nov 2020
DOIs
StatePublished - Dec 2020

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH GmbH

Funding

M.A. thanks the Ministry of Aliyah and integration and the Bar‐Ilan President scholarship program for Ph.D. scholarship. M.A. thanks the Ministry of Aliyah and integration and the Bar-Ilan President scholarship program for Ph.D. scholarship.

FundersFunder number
Ministry of Aliyah and integration
Ministry of Aliyah and Immigrant Absorption

    Keywords

    • chiral auxiliaries
    • chiral polymers
    • chirality
    • enantioselective crystallization
    • poly amino acids

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