Photochemically Removable Protecting Groups Based on Electrocyclic Reactions

基于电环反应的光化学可去除保护基团

• 批准号: 1055339
• 负责人: Mark Steinmetz
• 金额: $ 45万
• 依托单位: Marquette University
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2011
• 资助国家: 美国
• 起止时间: 2011-09-15 至 2015-08-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1055339&HistoricalAwards=false
• 关键词: Photochemically; Removable; Protecting; Groups; Based

The Chemical Structure, Dynamics and Mechanisms Program in the Chemistry Division at the National Science Foundation supports Professor Mark Steinmetz of Marquette University for synthesis and investigation of biological activity of photoreleased anionic metabolites. The goal of the research is to develop a series of robust caged benzothiophene carboxamides that, when exposed to long wavelength visible light, will undergo a 6-pi electrocyclic ring closing reaction that simultaneously expels an anion of biological importance. This controlled release can be used to manipulate the metabolite levels, pH, and/or the redox states inside cells. The methodology can be extended to create photo-removable protective groups in organic synthesis and in the synthesis of bio-oligomers.Broader impacts of the research include the multidisciplinary training opportunities for students, from organic synthesis to photochemistry and assessing the regulation of cellular processes via metabolic uptake. There are potential benefits to chemistry, biology, and medical science because of the generality of the methodology and the potential for temporal and spatial controlled release, for example, of ions across membranes through ion channels. Professor Steinmetz has an excellent track record of ethnic diversity in his research group.

国家科学基金会化学部的化学结构、动力学和机制项目支持马奎特大学的Mark Steinmetz教授合成和研究光释放阴离子代谢物的生物活性。该研究的目标是开发一系列坚固的笼状苯并噻吩甲酰胺，当暴露于长波长可见光时，将发生6-pi电环闭环反应，同时排出具有生物重要性的阴离子。这种受控释放可用于操纵细胞内的代谢物水平、pH和/或氧化还原状态。该方法可以扩展到在有机合成和生物低聚物合成中创建光可去除的保护基团。该研究的更广泛影响包括为学生提供多学科培训机会，从有机合成到光化学，以及通过代谢吸收评估细胞过程的调节。由于该方法的通用性和时间和空间受控释放的潜力，例如，离子通过离子通道跨膜释放，因此对化学、生物学和医学科学有潜在的益处。斯坦梅茨教授在他的研究小组中有着种族多样性的出色记录。