Development of New Strategies for the Synthesis of Bacterial Carbohydrates

凭借这一奖项，化学系的化学合成项目正在支持威斯康星大学麦迪逊分校制药科学系的唐卫平教授开发一种系统的方法，从常见的前体制造细菌碳水化合物。碳水化合物在炎症、感染、癌症转移和许多其他基本重要的生物过程中起着重要作用。开发从简单、常见的原料合成细菌碳水化合物的有效方法，对于研究涉及这些化合物的生物过程具有重要价值。不幸的是，细菌合成碳水化合物所用的几百种基本成分并不容易获得；这与人类和其他哺乳动物形成鲜明对比，它们只使用不到12个这样的积木。细菌碳水化合物需要单独合成，然后连接成低聚物，这是一个耗时且具有技术挑战性的过程。唐教授和他的研究团队正在开发合成策略，以解决这一障碍，并简化制造这些重要化合物的过程。这些研究还为研究生和博士后研究人员，以及传统上在STEM学科中代表性不足的年轻一代学生提供了科学培训。唐教授积极参与多个合作项目，让本科生和高中生参与学术研究，培养对科学的终身欣赏。Tang研究小组正在开发新的合成策略，系统地制备各种具有高度立体控制糖苷键的细菌碳水化合物。在一个重点领域，过渡金属催化的C-H胺化方法正被优化用于合成氨基糖及其衍生物。同时，这项研究也为如何在复杂环境中使用C-H胺化反应提供了见解。在第二个重点领域，烯烃功能化后的烯酮立体选择性还原为稀有脱氧糖提供了一条途径。这些研究同时推动了糖科学和合成有机化学的发展，同时促进了细菌中重要生物过程的研究。该项目也在多个层面上影响着化学教育：研究生可以获得合成专业知识，并参与指导活动，为他们在工业界和学术界的领导地位做准备，而本科生和高中生则可以获得实践经验和接触前沿研究。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。

With this award, the Chemical Synthesis Program of the Division of Chemistry is supporting Professor Weiping Tang of the Pharmaceutical Sciences Division of the University of Wisconsin-Madison to develop a systematic way to make bacterial carbohydrates from common precursors. Carbohydrates play important roles in inflammation, infection, cancer metastasis, and many other fundamentally important biological processes. The development of efficient methods to synthesize bacterial carbohydrates from simple, common starting materials is of value for the study of biological processes that involve these compounds. Unfortunately, bacteria use several hundred building blocks for carbohydrate synthesis that are not readily available; this is in contrast to humans and other mammals that use fewer than a dozen such building blocks. Bacterial carbohydrates need to be individually synthesized and then linked into oligomers, which is a time-consuming and technically challenging process. Professor Tang and his research team are developing synthetic strategies to address this roadblock and streamline the process for making these important compounds. These studies are also providing scientific training to graduate students and postdoctoral researchers, as well as younger generations of students traditionally underrepresented in STEM disciplines. Professor Tang actively participates in several collaborations where undergraduate and high school students partake in academic research and develop a lifelong appreciation for science. The Tang Research group is developing de novo synthesis strategies to systematically prepare a variety of bacterial carbohydrates with a high degree of stereocontrol over the glycosidic bond. In one focus area, a transition metal-catalyzed C-H amination approach is being optimized for the synthesis aminosugars and their derivatives. Simultaneously, this investigation is also providing insight in how to use C-H amination reactions in complex settings. In a second focus area, stereoselective reduction of enones followed by olefin functionalization is providing a route to rare deoxy sugars. These studies are simultaneously advancing glycoscience and synthetic organic chemistry while facilitating the study of important biological processes in bacteria. The program is also impacting chemical education at multiple levels: graduate students area gaining synthetic expertise and participating in mentoring activities that prepare them for leading positions in industry and academia, and underrepresented undergraduate and high school students and gaining hands-on experience and exposure to cutting-edge research.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.