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Stereoselective Synthesis of Biologically Relevant Heterocycles via Brønsted Acid Catalysis

Award Number: R15GM141981
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)
PERIOD OF PERFORMANCE START DATE: 06/01/2021
PERIOD OF PERFORMANCE END DATE: 05/31/2025

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Stereoselective Synthesis of Biologically Relevant Heterocycles via Brønsted Acid Catalysis - PROJECT SUMMARY The goal of this proposal is to generate innovative strategies for the asymmetric preparation of different heterocyclic motifs, including N-containing compounds, that contain a chiral center. Realization of this goal is expected to benefit medicinal chemistry campaigns because >59% of FDA approved drugs include a nitrogen- containing ring system and >56% of FDA approved drugs contain a stereogenic center, the absolute configuration of which is often critical to the activity of the molecule. To induce asymmetry in the proposed processes, a Brønsted acid will be used to catalyze a stereoselective cyclization reaction, with a focus on the use of commercially available chiral phosphoric acids. We hypothesize that the chiral phosphoric acid will complex with the starting hydroxy and amino esters and nitriles to initiate a cyclization reaction that preferentially generates one product enantiomer over the other. Our methods rapidly build complex molecules under mild conditions, and our research will result in a significant advance over current state of the art. Preliminary results support the validity of our approach and we will offer insight into the potential uses of the generated products. The ring structures we will prepare are ideal candidates for further manipulation into other biologically relevant structures or for diversification and evaluation themselves. Notably, these investigations will be advanced primarily by M.S. and undergraduate student researchers.


Issue Date FY	Funding FY	Legal Entity Name	Legal Entity Address	Legal Entity City	Legal Entity State	Legal Entity Zip Code	Legal Entity COUNTY	Legal Entity COUNTRY	Assistance Listing	Award Code	Budget Year	Action Date	Action Type	Action Amount

Issue Date FY: 2025 ( Subtotal = -$165 )
2025	2021	UNIVERSITY OF NORTH CAROLINA AT GREENSBORO	1000 SPRING GARDEN ST	GREENSBORO	NC	27412	GUILFORD	USA	Biomedical Research and Research Training	000	1	9/29/2025	NEW	-$165
														Subtotal = -$165

Issue Date FY: 2024 ( Subtotal = $0 )
2024	2021	UNIVERSITY OF NORTH CAROLINA AT GREENSBORO	1000 SPRING GARDEN ST	GREENSBORO	NC	27412	GUILFORD	USA	Biomedical Research and Research Training	000	1	5/31/2024	NEW	$0
														Subtotal = $0

Issue Date FY: 2021 ( Subtotal = $396,040 )
2021	2021	UNIVERSITY OF NORTH CAROLINA AT GREENSBORO	1000 SPRING GARDEN STREET	GREENSBORO	NC	27412	GUILFORD	USA	Biomedical Research and Research Training	000	1	5/4/2021	NEW	$396,040
														Subtotal = $396,040

Grand Total All Awards = $395,875

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Stereoselective Synthesis of Biologically Relevant Heterocycles via Brønsted Acid Catalysis

Award Number: R15GM141981

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)

PERIOD OF PERFORMANCE START DATE: 06/01/2021

PERIOD OF PERFORMANCE END DATE: 05/31/2025

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