Development of Photolabile Protecting Groups and Photochromic Systems Based on Intramolecular Excited State Proton Transfer

基于分子内激发态质子转移的光不稳定保护基团和光致变色体系的开发

• 批准号: 0842590
• 负责人: Vladimir Popik
• 金额: $ 39.15万
• 依托单位: University of Georgia Research Foundation Inc
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2009
• 资助国家: 美国
• 起止时间: 2009-09-01 至 2012-08-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0842590&HistoricalAwards=false
• 关键词: Development; Photolabile; Protecting; Groups; Photochromic

The Organic and Macromolecular Chemistry Program in the Chemistry Division at the National Science Foundation supports Professor Vladimir V. Popik of the University of Georgia who proposes to develop a new family of photolabile protecting groups (PPGs) based on photochemical elimination of substrates from o-hydroxybenzyl alcohol derivatives. Preliminary results suggest that PPGs based on this reaction, while generally applicable, are especially suitable for the direct caging of alcohols. This new PPG platform will also be investigated for the photolabile protection of glycols, carbohydrates, and carbonyl compounds. PPGs developed in this project are expected to have long shelf-life and good hydrolytic stability in the dark, as well as high quantum and chemical yield of photo-deprotection. Substrate release from the newly-developed PPGs is expected to be fast enough to allow for spatial- and time-resolved biochemical studies. The mechanism and dynamics of the cleavage reaction will be studied in detail to assist us in the design of novel PPGs.Broader impacts of the proposed research will contribute new caging tools to organic synthesis, biochemistry, and medical technology. PPGs and photochromic systems developed in this work might serve as a basis for the design of new drugs and drug delivery systems that can be photoactivated, as well as open new approaches to photolithography and information recording. This project will provide undergraduate and graduate students with interdisciplinary training on the interface of synthetic, physical organic chemistry, and photochemistry. Students from underrepresented groups will be recruited to work on this project. A photochemical laboratory will be established, which will provide the University of Georgia and local scientists with apparatus and expertise to conduct photochemical experiments. The interdisciplinary nature of the research is expected to produce extensive collaboration with other research groups, both locally and internationally.

国家科学基金会化学部的有机和大分子化学计划支持佐治亚大学的Vladimir V. Popik教授，他建议基于光化学的o-羟基苯二苯二苯甲油醇衍生物的基质消除光化学消除基质。初步结果表明，基于此反应的PPGS虽然通常适用，尤其适用于直接凝结醇。该新的PPG平台还将进行研究，以保护乙二醇，碳水化合物和羰基化合物的光片保护。预计在该项目中开发的PPG将在黑暗中具有长期的保质期和良好的水解稳定性，以及光养分的高量子和化学产率。从新开发的PPG中释放的底物释放有望足够快，可以进行空间和时间分辨的生化研究。裂解反应的机制和动力学将进行详细研究，以帮助我们设计新颖的PPG。拟议研究的Broader影响将为有机合成，生物化学和医疗技术贡献新的笼子工具。这项工作中开发的PPG和光致变色系统可能是可以光活化的新药物和药物输送系统设计的基础，以及开放的新方法来看光刻和信息记录。该项目将为本科生和研究生提供有关合成，物理有机化学和光化学界面的跨学科培训。来自代表性不足的小组的学生将被招募来从事该项目。将建立一个光化学实验室，该实验室将为佐治亚大学和当地科学家提供设备和专业知识，以进行光化学实验。该研究的跨学科性质有望与当地和国际的其他研究小组进行广泛的合作。