Light-directed derivatization, caging, and releasing methodologies based on o-quinone methide chemistry

有了这个奖项，化学部的化学合成计划资助教授弗拉基米尔Popik的化学系在格鲁吉亚大学设计和合成新型紫外线和近红外敏感的光不稳定的保护基团和光可裂解的连接器，以及开发方法的选择性光衍生化和释放硫醇部分在各种基板。光不稳定的保护基团允许时空控制底物活化，以及“无试剂”脱保护。使用可见光谱红边的光释放活性化合物扩展了生物学中“笼”技术的实用性，因为它最大限度地减少了对细胞的光损伤，并可能用于哺乳动物组织的实验。该项目旨在为有机，生物和药物化学家提供新的工具来控制笼状化合物在时间和空间上的活性，具有潜在的广泛应用。 例如，蛋白质中天然或遗传工程改造的半胱氨酸残基的选择性和可逆衍生化可以允许远程控制其活性。可逆固定可用于传感器阵列的修饰或修复。该项目将为本科生和研究生，包括那些来自历史上在科学中代表性不足的群体的学生，提供合成和物理有机化学界面的跨学科培训，以及光化学，生物化学和材料科学的元素。

With this award, the Chemical Synthesis Program of the Chemistry Division is funding Professor Vladimir Popik of the Department of Chemistry at the University of Georgia to design and synthesize novel UV and NIR-sensitive photolabile protecting groups and photocleavable linkers, as well as develop methods for the selective photo-derivatization and release of thiol moieties in various substrates. Photolabile protecting groups allow for the spatiotemporal control of substrate activation, as well as for 'reagentless' deprotection. Release of active compounds using light at the red edge of the visible spectrum extends the utility of the 'caging' technique in biology as it minimizes photo-damage to cells and might be useful for experiments in mammalian tissues.. This project aims to provide organic, biological, and medicinal chemists with new tools to control activity of caged compounds in time and in space, with potentially broad application. For example, the selective and reversible derivatization of native or genetically engineered cysteine residues in proteins may allow for the remote control of their activity. Reversible immobilization can be useful for modification or repair of sensor arrays. This project will provide undergraduate and graduate students, including those from groups historically underrepresented in the sciences, with interdisciplinary training at the interface of synthetic and physical organic chemistry, with elements of photochemistry, biochemistry, and material science.