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Selective Nitrogen Atom Transfer for Applications in Biomedical Sciences

Award Number: R01GM110382
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: 05/01/2014
PERIOD OF PERFORMANCE END DATE: 02/28/2023

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Selective Nitrogen Atom Transfer for Applications in Biomedical Sciences - DESCRIPTION (provided by applicant): Numerous pharmaceuticals contain at least one nitrogen atom and many of those nitrogen atoms are directly attached to stereogenic centers. Therefore, synthetic methods that incorporate selective nitrogen atom transfer to readily available hydrocarbons are important tools for the synthesis of these valuable molecules. While methods for selective olefin aziridination and direct C-H amination are well-established, methods for direct difunctionalization of olefins with a nitrogen atom and a range of heteroatom-based functional groups are less explored yet critically important to organic synthesis and its applications to the biomedical sciences. In particular, a general and selective nitrogen atom transfer approach that can achieve the aminohydroxylation, aminofluorination, and aminohalogenation of a wide variety of olefins has yet to be discovered. Our long-term goal is to develop selective and general nitrogen atom transfer methods that directly difunctionalize a wide variety of olefins with a nitrogen and a range of heteroatom-based functional groups. The objective of the proposed research is to develop a series of iron-catalyzed nitrogen atom transfer methods for direct olefin difunctionalization with an emphasis on aminohydroxylation, aminofluorination, and aminohalogenation. Based upon our preliminary discoveries, our underlying hypothesis is that a unique iron- nitrenoid can be modulated to mediate a range of olefin difunctionalization reactions rather than only precedent aziridination and C-H amination reactions. The proposed research will explore this hypothesis in the context of two Specific Aims. First, we plan to develop iron-catalyzed, selective aminohydroxylation methods that will incorporate a variety of olefin and heteroarene substrates for synthesis of amino alcohols and b-hydroxyl amino acids. Second, we will develop iron-catalyzed, selective aminofluorination and aminohalogenation methods for a range of olefins that will afford b-fluoro, chloro, and bromo amines as well as b-fluoro and chloro amino acids. The proposed approach is innovative because it explores the new reactivity of an iron-nitrenoid in a context that significantly departs from the established reactivity of metal-nitrenoids. The proposed research is significant because it will lay the foundation for the development of a wide range of methods for selective olefin difunctionalization from the same type of reactive intermediate generated from a first-row transition metal. Completion of the proposed research will provide an array of unique olefin difunctionalization methods that would become valuable tools for medicinal chemists. Furthermore, it will also produce a variety of valuable synthetic building blocks and biologically important molecules that will accelerate the basic biomedical and clinical research.


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: 2023 ( Subtotal = -$6,926 )
2023	2018	BRANDEIS UNIVERSITY	415 SOUTH ST	WALTHAM	MA	02453	MIDDLESEX	USA	Biomedical Research and Research Training	000	6	8/23/2023	CHANGE OF GRANTEE / TRAINING INSTITUTION / AWARDING INSTITUTION	-$6,926
														Subtotal = -$6,926

Issue Date FY: 2022 ( Subtotal = $0 )
2022	2018	BRANDEIS UNIVERSITY	415 SOUTH ST	WALTHAM	MA	02453	MIDDLESEX	USA	Biomedical Research and Research Training	000	6	3/14/2022	CHANGE OF GRANTEE / TRAINING INSTITUTION / AWARDING INSTITUTION	$0
														Subtotal = $0

Issue Date FY: 2021 ( Subtotal = -$53,181 )
2021	2019	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Extramural Research Restoration Program: Hurricanes Harvey, Maria, and Irma – non-construction	002	5	1/25/2021	SUPPLEMENT FOR EXPANSION	-$53,181
2021	2018	BRANDEIS UNIVERSITY	415 SOUTH ST	WALTHAM	MA	02453	MIDDLESEX	USA	Biomedical Research and Research Training	001	6	1/25/2021	CHANGE OF GRANTEE / TRAINING INSTITUTION / AWARDING INSTITUTION	$37,296
2021	2018	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	000	5	1/25/2021	NON-COMPETING CONTINUATION	-$37,296
														Subtotal = -$53,181

Issue Date FY: 2020 ( Subtotal = $14,000 )
2020	2019	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Extramural Research Restoration Program: Hurricanes Harvey, Maria, and Irma – non-construction	003	5	6/12/2020	SUPPLEMENT FOR EXPANSION	$0
2020	2019	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	004	5	6/12/2020	SUPPLEMENT FOR EXPANSION	-$85,280
2020	2019	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	001	5	2/21/2020	SUPPLEMENT FOR EXPANSION	$0
2020	2018	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	002	5	6/12/2020	NON-COMPETING CONTINUATION	-$142,000
2020	2018	BRANDEIS UNIVERSITY	415 SOUTH ST	WALTHAM	MA	02453	MIDDLESEX	USA	Biomedical Research and Research Training	005	6	6/12/2020	CHANGE OF GRANTEE / TRAINING INSTITUTION / AWARDING INSTITUTION	$241,280
2020	2018	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	000	5	2/21/2020	NON-COMPETING CONTINUATION	$0
														Subtotal = $14,000

Issue Date FY: 2019 ( Subtotal = $379,780 )
2019	2019	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Extramural Research Restoration Program: Hurricanes Harvey, Maria, and Irma – non-construction	000	5	6/24/2019	SUPPLEMENT FOR EXPANSION	$294,500
2019	2019	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	001	5	8/28/2019	SUPPLEMENT FOR EXPANSION	$85,280
														Subtotal = $379,780

Issue Date FY: 2018 ( Subtotal = $281,200 )
2018	2018	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	001	5	5/15/2018	NON-COMPETING CONTINUATION	$28,120
2018	2018	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	000	5	2/13/2018	NON-COMPETING CONTINUATION	$253,080
														Subtotal = $281,200

Issue Date FY: 2017 ( Subtotal = $281,200 )
2017	2017	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE SE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	000	4	2/10/2017	NON-COMPETING CONTINUATION	$253,080
2017	2017	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.	58 EDGEWOOD AVE NE 3RD FL	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	001	4	6/21/2017	NON-COMPETING CONTINUATION	$28,120
														Subtotal = $281,200

Issue Date FY: 2016 ( Subtotal = $380,377 )
2016	2016	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION	33 GILMER STREET SOUTHEAST	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	001	3	7/14/2016	SUPPLEMENT FOR EXPANSION	$99,177
2016	2016	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION	33 GILMER STREET SOUTHEAST	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	000	3	2/17/2016	NON-COMPETING CONTINUATION	$281,200
														Subtotal = $380,377

Issue Date FY: 2015 ( Subtotal = $281,200 )
2015	2015	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION	33 GILMER STREET SOUTHEAST	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	000	2	2/19/2015	NON-COMPETING CONTINUATION	$281,200
														Subtotal = $281,200

Issue Date FY: 2014 ( Subtotal = $281,200 )
2014	2014	GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION	33 GILMER STREET SOUTHEAST	ATLANTA	GA	30303	FULTON	USA	Biomedical Research and Research Training	000	1	4/10/2014	NEW	$281,200
														Subtotal = $281,200

Grand Total All Awards = $1,838,850

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Selective Nitrogen Atom Transfer for Applications in Biomedical Sciences

Award Number: R01GM110382

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: 05/01/2014

PERIOD OF PERFORMANCE END DATE: 02/28/2023

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