Enantioselective Fluorescent Recognition of Amino Alcohols and Catalyst Screening

该项目由弗吉尼亚大学化学系化学结构、动力学和机理b项目资助，由林璞教授开发用于识别手性有机分子的新型分子传感器。这些传感器可用于促进非对称反应的高通量筛选。由于这些不对称反应广泛应用于精细化学制剂，如药物及其中间体，这些传感器可以提高其制备效率，并可能降低成本。在这个项目中，学生和其他研究人员接受不同领域的教育和培训，包括有机化学、分析化学和材料化学。研究小组还积极开展面向K-12学生的科学技术拓展活动。设计并合成了用于对映选择性荧光识别的高氟分子探针。这些探针可以与目标手性底物形成共价键，并将其带入氟相进行荧光检测。当这些材料用于筛选不对称反应时，它们对反应产物的荧光响应可以在氟相中测量，这可以最大限度地减少反应介质中其他组分的干扰，因为正常的有机和无机材料不能溶解在氟相中。与传统的基于色谱的方法相比，这种荧光测量方法可能更快，更适合于高通量分析。这一策略可以促进手性化合物不对称合成的手性催化剂和试剂的发现，在生物化学、制药和农业等领域具有广泛的应用。该奖项反映了美国国家科学基金会的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

In this project, funded by the Chemical Structure, Dynamics and Mechanisms-B Program of the Chemistry Division, Professor Lin Pu of the Department of Chemistry at University of Virginia is developing new molecular sensors for the recognition of chiral organic molecules. These sensors can be used to facilitate high throughput screening of asymmetric reactions. As these asymmetric reactions are widely used in fine chemical preparations such as pharmaceutical drugs and their intermediates, these sensors can increase the efficiency of their preparation and perhaps reduce cost. In this project, students and other researchers receive education and training in diverse areas including organic, analytical, and materials chemistry. The research team is also active in outreach activities to K-12 students in science and technology. The molecular probes of high fluorine contents are being designed and synthesized for enantioselective fluorescent recognition. These probes can form covalent bonds with the targeted chiral substrates and bring them into the fluorous phase for fluorescent detection. When these materials are used to screen asymmetric reactions, their fluorescence responses toward the reaction products can be measured in the fluorous phase, and this may minimize the interference from other components in the reaction media since normal organic and inorganic materials cannot be dissolved in the fluorous phase. In comparison to the traditional chromatography-based methods, this fluorescence measurement method may be much faster and more well suited to high throughput analysis. This strategy could facilitate the discovery of chiral catalysts and reagents for the asymmetric synthesis of chiral compounds with diverse applications in areas such as biochemical, pharmaceutical and agricultural industries.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.