| NSF Org: |
CHE Division Of Chemistry |
| Recipient: |
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| Initial Amendment Date: | March 10, 2014 |
| Latest Amendment Date: | March 10, 2014 |
| Award Number: | 1352587 |
| Award Instrument: | Standard Grant |
| Program Manager: |
Tarek Sammakia
CHE Division Of Chemistry MPS Directorate for Mathematical and Physical Sciences |
| Start Date: | April 1, 2014 |
| End Date: | March 31, 2019 (Estimated) |
| Total Intended Award Amount: | $600,000.00 |
| Total Awarded Amount to Date: | $600,000.00 |
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| Recipient Sponsored Research Office: |
10550 N TORREY PINES RD LA JOLLA CA US 92037-1000 (858)784-8653 |
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| Primary Place of Performance: |
10550 North Torrey Pines Road La Jolla CA US 92037-1000 |
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Performance Congressional District: |
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| Unique Entity Identifier (UEI): |
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| NSF Program(s): | Chemical Synthesis |
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| Award Agency Code: | 4900 |
| Fund Agency Code: | 4900 |
| Assistance Listing Number(s): | 47.049 |
ABSTRACT
With this CAREER award, the Chemical Synthesis Program is supporting the research and educational efforts of Dr. Ryan A. Shenvi of the Department of Chemistry at the Scripps Research Institute. The focus of this research is to develop a new class of stereoselective nucleophilic displacement reactions that operate on isolated tertiary carbon centers through attack of unstabilized carbocationic contact ion pairs. This research fills a major methodological gap in chemical synthesis that has been recognized for nearly 100 years. Realization of the goals of this proposal would broadly impact the synthesis of challenging tert-alkyl-substituted chiral materials that are difficult or impossible to access by other methods. A successful outcome of the research proposed here entails the reaction of unstabilized carbocations and various nucleophiles with high chemo- and stereoselectivity, which has important consequences for the production of materials for the interfacing fields of biology, medicine, and physics.
The key focus of this research is on the development of concise and scalable syntheses of therapeutically relevant molecules through the invention of new chemical reactions that allow a degree of complexity which has been unachievable through standard methods. The proposed research will potentially allow ready access to a number of important natural and unnatural products while reducing the number of steps and increasing the efficiency. The educational component of this grant involves curriculum development and outreach through the Scripps SURF program. This effort involves the development of a curriculum for high-school, undergraduate, and graduate education that articulates the scientific method in the context of organic chemistry research.
PROJECT OUTCOMES REPORT
Disclaimer
This Project Outcomes Report for the General Public is displayed verbatim as submitted by the Principal Investigator (PI) for this award. Any opinions, findings, and conclusions or recommendations expressed in this Report are those of the PI and do not necessarily reflect the views of the National Science Foundation; NSF has not approved or endorsed its content.
Chemistry is the science of transforming matter. Our laboratory invents new chemical reactions to build complex molecules from simple chemicals. Molecular complexity in drugs can impart specificity and limit side-effects. However, the synthesis of complex molecules requires many iterative chemical reactions, which can be costly, time-consuming and wasteful. Therefore, we develop new reactions to lower costs, accelerate synthesis and generate less chemical waste. Our NSF-supported project began with the investigation of an unusual chemical reaction that converted naturally occurring alcohols from plants into rare marine sponge-derived metabolites that have shown promise for the treatment of malaria. We aimed to extend this reactivity to highly hindered molecules that cannot be accessed economically. Ultimately, we discovered a reaction that could merge two cyclic (ring-like) molecules and, despite extreme crowding at the bond that held them together, the reaction occurred very quickly, in less than one second. Expanding this idea to different building blocks has delivered a new general chemical reaction that makes unusual molecular architecture. Assay of these unusual molecules against a variety of biological targets identified potential leads for the treatment of inflammation and auto-immune disease. This discovery completed a journey from basic chemistry research to identification of a potential new medicine and began a new journey to translate this discovery into a drug.
Last Modified: 04/25/2019
Modified by: Ryan Shenvi
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