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Characterization of chiral interactions by fluorescence anisotropy and development of fluorescence sensors for recognition of molecular species.

机译：通过荧光各向异性表征手性相互作用以及开发用于识别分子种类的荧光传感器。

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摘要

Enantioselective separation is a major concern in the fields of drug development and enantioselective synthesis. Hence, there is need for simple, fast, reliable and sensitive techniques to evaluate chiral interactions. In this work, steady-state fluorescence anisotropy was used to characterize chiral interactions using fluorescent enantiomer pairs with various chiral selectors. Preliminary studies have shown fluorescence anisotropy to be an effective tool for evaluating chiral recognition. In Chapter 2, four chiral selectors were examined to explore correlation between separation and anisotropy ratio of enantiomers under similar conditions. A strong correlation between separation and fluorescence anisotropy data was observed, prompting an investigation into the feasibility of using fluorescence anisotropy to predict optimal conditions for chiral separations in HPLC. In Chapter 3, chiral interactions of slurries of five chiral phases and several enantiomers were examined as a function of temperature and solvent composition and the feasibility of predicting optimal conditions for chiral separations was discussed. Comparison of fluorescence anisotropy and published liquid chromatographic data of 1'1-bi-2-naphthol on a Kromasil chiral phase under similar conditions showed that the fluorescence results were consistent with those obtained from HPLC experiments. In Chapter 4, chiral interactions of propranolol with three Kromasil chiral phases were evaluated and the chiral recognition process was found to be different.; In a second project, the development of fluorescent sensors for molecular species was addressed. An evaluation of the binding response of fluorescent photoinduced electron transfer (PET) sensors to three carboxylate anions was presented in Chapter 6. One of the sensors showed a binding response to the anions under physiological conditions while the other responded only in organic media. In Chapter 7, the fluorescence sensing ability of a trans-stilbene derivative exploits conformational quenching was examined. Its fluorescence intensity increased as a function of viscosity proving the effect of restricted rotation on its sensing ability. Chapter 8 discusses the results of studies that showed selectivity and strong binding for Zn2+ compared to Ca2+, Mg2+ and Hg2+.
机译：对映选择性分离是药物开发和对映选择性合成领域中的主要关注。因此，需要简单，快速，可靠和敏感的技术来评价手性相互作用。在这项工作中，稳态荧光各向异性被用来表征具有各种手性选择剂的荧光对映体对的手性相互作用。初步研究表明，荧光各向异性是评估手性识别的有效工具。在第二章中，研究了四个手性选择剂，以探索相似条件下对映异构体的分离与各向异性比率之间的相关性。观察到分离和荧光各向异性数据之间存在很强的相关性，这促使人们开始研究使用荧光各向异性预测HPLC中手性分离的最佳条件的可行性。在第三章中，考察了五个手性相和几种对映体的浆液的手性相互作用，该手性是温度和溶剂组成的函数，并讨论了预测最佳手性分离条件的可行性。在相似条件下，在Kromasil手性相上的1'1-bi-2-萘酚的荧光各向异性和已公开的液相色谱数据的比较表明，荧光结果与HPLC实验获得的结果一致。在第四章中，对心得安与三个Kromasil手性相的手性相互作用进行了评估，发现手性识别过程不同。在第二个项目中，解决了用于分子物种的荧光传感器的开发。第6章介绍了荧光光电诱导电子转移（PET）传感器对三种羧酸根阴离子的结合反应的评估。一种传感器在生理条件下显示出对阴离子的结合反应，而另一种仅在有机介质中反应。在第七章中，研究了反式二苯乙烯衍生物利用构象猝灭的荧光传感能力。其荧光强度随粘度增加而增加，证明了旋转受限对其感测能力的影响。第8章讨论了研究结果，这些研究表明与Ca2 +，Mg2 +和Hg2 +相比，Zn2 +具有选择性和强结合性。

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  • 作者

    Kimaru, Irene W.;

  • 作者单位

    Southern Illinois University at Carbondale.;

  • 授予单位 Southern Illinois University at Carbondale.;
  • 学科 Chemistry Analytical.
  • 学位 Ph.D.
  • 年度 2006
  • 页码 250 p.
  • 总页数 250
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
  • 关键词

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