Design of chiral acidic molecularly imprinted polymer for the enantioselective separation of (±)-DOPA

IF 2.8 4区 生物学 Q3 BIOTECHNOLOGY & APPLIED MICROBIOLOGY Journal of chemical technology and biotechnology Pub Date : 2024-06-10 DOI:10.1002/jctb.7691
Rua B Alnoman
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Abstract

Background

The study focuses on developing a stable enantioselective matrix for the efficient chiral identification and enantioresolution of l-DOPA and (±)-DOPA. The matrix is derived from a copolymeric material made from poly[(vinylsulfonic acid)-co-(4-vinylpyridine)] crosslinked with divinylbenzene.

Results

l-DOPA-vinylsulfonamide was synthesized and characterized. This chiral sulfonamide was copolymerized with 4-vinylpyridine in the presence of a divinylbenzene crosslinker, using azobisisobutyronitrile as a thermal initiator. Post-polymerization, the polymeric particles were treated with NaOH and subsequently washed with acid to remove the integrated l-DOPA species. Scanning electron microscopy and Fourier transform infrared spectroscopy confirmed the imprinted l-DOPA-IP particles. The manufactured l-DOPA-IP demonstrated a tenfold greater affinity for l-DOPA compared to d-DOPA. Langmuir adsorption experiments at pH 6 showed a maximum capacity of 162 mg g−1. Enantiomeric excess values for l- and d-DOPA, determined through optical separation using a column approach, were 94% and 82%, respectively, in the loading and recovery solutions.

Conclusion

The developed copolymeric material effectively served as an enantioselective matrix, exhibiting high selectivity and capacity for l-DOPA. The process demonstrated efficient chiral identification and separation, achieving significant enantiomeric excess values for both l- and d-DOPA. © 2024 Society of Chemical Industry (SCI).

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设计用于(±)-DOPA 对映体选择性分离的手性酸性分子印迹聚合物
这项研究的重点是开发一种稳定的对映体选择性基质,用于 l-DOPA 和 (±)-DOPA 的高效手性鉴定和对映体解析。该基质由聚[(乙烯基磺酸)-共(4-乙烯基吡啶)]与二乙烯基苯交联的共聚物材料制成。以偶氮二异丁腈为热引发剂,这种手性磺酰胺在二乙烯基苯交联剂存在下与 4-乙烯基吡啶共聚。聚合后,用 NaOH 处理聚合颗粒,然后用酸清洗,以除去其中的 l-DOPA 物质。扫描电子显微镜和傅立叶变换红外光谱证实了压印的 l-DOPA-IP 颗粒。与 d-DOPA 相比,制成的 l-DOPA-IP 对 l-DOPA 的亲和力高出十倍。在 pH 值为 6 的条件下进行的朗缪尔吸附实验显示,其最大吸附容量为 162 mg g-1。通过使用色谱柱方法进行光学分离测定的 l-DOPA 和 d-DOPA 对映异构体过量值在加载溶液和回收溶液中分别为 94% 和 82%。该工艺展示了高效的手性识别和分离能力,使 l- 和 d-DOPA 的对映体过量值显著提高。© 2024 化学工业协会(SCI)。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
CiteScore
7.00
自引率
5.90%
发文量
268
审稿时长
1.7 months
期刊介绍: Journal of Chemical Technology and Biotechnology(JCTB) is an international, inter-disciplinary peer-reviewed journal concerned with the application of scientific discoveries and advancements in chemical and biological technology that aim towards economically and environmentally sustainable industrial processes.
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