With this award, the Chemical Synthesis Program of the NSF Division of Chemistry is funding the research of Professor Jacquelyn Gervay-Hague who is developing efficient continuous flow methods to make site-specific changes of polyhydroxylic natural products, such as sugars. Continuous flow chemistry is a process in which reactants are mixed together into tubes allowing a chemical reaction to occur under precisely controlled conditions where numerous reaction conditions can be adjusted. This method is of increasing importance in the chemical industry where it is used in multi-step processes leading to the efficient production of pharmaceuticals and other value-added chemicals. With the careful experimental control offered by this technology, the reaction conditions such as temperature, pressure, and reaction time result in new relationships between chemical structure and reactivity that are not observable in traditional "one-pot" chemistry synthesis. Students involved in this research are investigating complex chemical reactions providing them the opportunity to express their own creative design of making natural products. The use of Nuclear Magnetic Resonance (NMR) spectroscopy as a major tool for predicting chemical reactivity gives further insight into the nature of chemical bonds and their inherent reactivity. This research provides a fertile learning platform for both doctoral and masters graduate students to launch scientific careers that benefit society through gainful employment in academic, entrepreneurial, and industrial settings in advanced manufacturing.

The intellectual merit of the research focuses on transferring successful batch chemistries to continuous flow reactions to increase selectivity, chemical diversity, and productivity with improved safety metrics. Importantly, microscale segmented flow techniques provide rapid assessment of product formation and enable continuous flow optimization as a basis for future automation. The ability to differentiate between seemingly equivalent hydroxyl groups in order to achieve specific functionalization is a major challenge for chemical synthesis development. Typically, several protection and deprotection steps are required, which increases production time and decreases step economy. In addition, many of the procedures require synthetic expertise, which limits accessibility to scientists outside the chemical synthesis arena. Automated synthesis platforms including peptide and nucleic acid synthesizers have been widely adopted by non-experts and have transformed chemical biology research. Increasing access of natural product analogs to biomedical researchers was proclaimed a top priority in a recent National Academy of Sciences publication on the future of glycosciences. This research developes continuous flow methodologies for site-specific conversion of silyl ethers to alternative functionalities such as esters, ethers, and alcohols.

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.

National Science Foundation (NSF)
Division of Chemistry (CHE)
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Jin Cha
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University of California Davis
United States
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