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Novel Acylborons and Alpha-hydroxy Borons to Enable Modular, Regio- and Stereocontrolled Synthesis of Bioactive Molecules and Protein Conjugates

Award Number: R35GM143091
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: 08/01/2021
PERIOD OF PERFORMANCE END DATE: 07/31/2027

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Novel Acylborons and Alpha-hydroxy Borons to Enable Modular, Regio- and Stereocontrolled Synthesis of Bioactive Molecules and Protein Conjugates - Project Summary/Abstract The long-term goal of my research laboratory is to establish strategies that allow the synthesis of previously inaccessible regio-/stereodefined organoborons to ultimately enable the lego-like construction of C(sp3)-rich bioactive molecules and protein conjugates. Modular synthetic strategies using interchangeable building blocks are expected to enable a generalized route to the targeted compound class which is crucial for optimizing its biological activity. Orthogonally functionalized vinylic or aromatic halo-organoborons have played a critical role in many modular synthetic routes to natural products. In contrast, strategies to construct multifunctional and stereodefined acylborons/alkyl boron building blocks and their applications for modular synthesis of C(sp3)-rich molecular scaffolds and bioconjugates remain underexplored. The research projects described in this proposal will provide a platform to achieve the above broader goal by establishing a versatile acylboron/alpha-hydroxy boron-based paradigm to open-up access to several unique organoborons having broad applications in medicinal chemistry and chemical biology. Acylborons represent an underexplored class of organoborons whose existence and remarkable synthetic utility is beginning to emerge only recently. We previously reported an unsymmetrical diboron-based approach to construct rare acylborons including the first example of an alpha,beta-unsaturated acyl boron. Our recent preliminary data suggests that alpha,beta-unsaturated acyl borons and alpha-hydroxy borons are powerful intermediates to access orthogonally functionalized, regio- and stereodefined organoborons. Building upon our published work and preliminary data, we will develop general methods for synthesis and application of several new types of multifunctional acylborons and alpha-hydroxy borons to ultimately provide enantioenriched organoborons that would be difficult to prepare using existing methods. We will demonstrate the unique benefit of these novel building blocks to install rare substitution patterns on bioactive molecules and to enable a modular synthetic approach to chiral frameworks found in medicinally important compounds. In a complementary research direction, we will develop a new class of mutually orthogonal bioconjugation agents that are expected to allow i) simultaneous probing of multiple protein- protein interactions and ii) preparation of homogeneous and stable bioconjugates.


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: 2026 ( Subtotal = $0 )
2026	2025	THE TRUSTEES OF THE STEVENS INSTITUTE OF TECHNOLOGY	ONE CASTLE POINT ON HUDSON	HOBOKEN	NJ	07030	HUDSON	USA	Biomedical Research and Research Training	000	5	5/7/2026	NON-COMPETING CONTINUATION	$0
														Subtotal = $0

Issue Date FY: 2025 ( Subtotal = $373,458 )
2025	2025	THE TRUSTEES OF THE STEVENS INSTITUTE OF TECHNOLOGY	ONE CASTLE POINT ON HUDSON	HOBOKEN	NJ	07030	HUDSON	USA	Biomedical Research and Research Training	000	5	7/30/2025	NON-COMPETING CONTINUATION	$373,458
														Subtotal = $373,458

Issue Date FY: 2024 ( Subtotal = $373,865 )
2024	2024	THE TRUSTEES OF THE STEVENS INSTITUTE OF TECHNOLOGY	1 CASTLEPOINT ON HUDSON	HOBOKEN	NJ	07030	HUDSON	USA	Biomedical Research and Research Training	000	4	7/24/2024	NON-COMPETING CONTINUATION	$373,865
														Subtotal = $373,865

Issue Date FY: 2023 ( Subtotal = $361,784 )
2023	2023	THE TRUSTEES OF THE STEVENS INSTITUTE OF TECHNOLOGY	1 CASTLEPOINT ON HUDSON	HOBOKEN	NJ	07030	HUDSON	USA	Biomedical Research and Research Training	000	3	6/27/2023	NON-COMPETING CONTINUATION	$361,784
														Subtotal = $361,784

Issue Date FY: 2022 ( Subtotal = $224,783 )
2022	2022	STEVENS INSTITUTE OF TECHNOLOGY (INC)	1 CASTLE POINT ON HUDSON	HOBOKEN	NJ	07030	HUDSON	USA	Biomedical Research and Research Training	000	2	7/19/2022	NON-COMPETING CONTINUATION	$224,783
														Subtotal = $224,783

Issue Date FY: 2021 ( Subtotal = $215,244 )
2021	2021	STEVENS INSTITUTE OF TECHNOLOGY (INC)	1 CASTLE POINT ON HUDSON	HOBOKEN	NJ	07030	HUDSON	USA	Biomedical Research and Research Training	000	1	7/16/2021	NEW	$215,244
														Subtotal = $215,244

Grand Total All Awards = $1,549,134

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Novel Acylborons and Alpha-hydroxy Borons to Enable Modular, Regio- and Stereocontrolled Synthesis of Bioactive Molecules and Protein Conjugates

Award Number: R35GM143091

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: 08/01/2021

PERIOD OF PERFORMANCE END DATE: 07/31/2027

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