Swirling to Asymmetric Catalysis: Development of PNA-Based Double Helical Catalysts

在这个由化学系化学合成项目资助的EAGER项目中，弗吉尼亚大学化学系林朴教授将探索开发基于肽核酸（PNAs）的新型双螺旋催化剂用于不对称催化。 与目前开发的用于不对称催化的催化剂相比，所提出的基于PNA的双螺旋催化剂可以具有几个优点。 例如，基于PNA的双链体可以放大并入的催化位点的手性信息以产生大分子双螺旋结构，其可以提供刚性、稳定和明确限定的螺旋腔用于有效的手性诱导。 此外，与使用DNA不同，使用合成的PNA使得两种螺旋构型容易用于手性分子的两种对映体的不对称合成。 这些大分子催化剂也可以通过过滤（非均相）或膜过滤（均相）容易地回收。 拟开展的PNA工作将利用化学生物学中开发的技术，发现用于不对称合成的新手性催化剂。 该项目的成功开发将对任何需要合成分子的活动领域产生影响，例如制药，化学，农业以及生物和化学研究活动。 将招募不同背景的研究生和本科生进行本项目中描述的研究。 因此，该项目将在有机合成、催化、手性化学和化学生物学等领域为这些研究人员提供广泛的教育和培训。 他们将学习许多对他们未来就业有用的实验室技能。 通过本项目的培训，学生可以成为新的创新者和专业研究人员，以进一步造福社会。

In this EAGER project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Lin Pu of the Department of Chemistry at University of Virginia will explore the development of peptide nucleic acids (PNAs)-based novel double helical catalysts for asymmetric catalysis. In comparison with the catalysts currently developed for asymmetric catalysis, the proposed PNA-based double helical catalysts could have several advantages. For example, the PNA-based duplexes could amplify the chiral information of the incorporated catalytic site to generate the macromolecular double helical structure which could provide rigid, stable, and well-defined helical cavities for efficient chiral induction. In addition, unlike the use of DNAs, using the synthetic PNAs makes both helical configurations readily available for the asymmetric synthesis of both enantiomers of a chiral molecule. These macromolecular catalysts can also be easily recovered by filtration (heterogeneous) or membrane filtration (homogeneous). The proposed work on PNAs will utilize the technology developed in chemical biology for the discovery of new chiral catalysts for asymmetric synthesis. Successful development of the project will have an impact on any area of activity in which the synthesis of molecules is needed, such as the pharmaceutical, chemical, agricultural industry, and the biological and chemical research activities. Graduate students and undergraduate students of diverse backgrounds will be recruited to conduct the research described in this project. Thus, this project will provide extensive education and training for these researchers in areas such as organic synthesis, catalysis, chiral chemistry and chemical biology. They will learn many laboratory skills that are useful for their future employment. After the training through this project, the students can become new innovators and professional researchers to further benefit the society.