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Development of Catalytic Glycosylations and Biologically Important Glycosaminoglycans

Award Number: R35GM149213
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: 09/01/2023
PERIOD OF PERFORMANCE END DATE: 08/31/2028

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Development of Catalytic Glycosylations and Biologically Important Glycosaminoglycans - PROJECT SUMMARY The work in this proposal builds on our expertise in catalytic stereoselective glycosylations to result in efficient synthetic methodologies for construction of the challenging glycosidic bonds. We recently discovered that readily available phenanthrolines, rigid and planar organic compound with two pyridine rings fused to a benzene ring, effectively act as nucleophilic catalysts to promote stereoselective 1,2- cis glycosylation reactions of alcohol nucleophiles with both pyranosyl and furanosyl bromide donors. The phenanthroline catalytic system provides efficient access to a myriad of 1,2-cis pyranosides and furanosides bearing the C2-oxygen, -azido and -fluoro functional groups under mild and operationally simple conditions. The phenanthroline-catalyzed methodologies represent long standing synthetic challenges for highly desirable glycosylations to generate biologically important oligosaccharides and glycopeptides to advance an understanding of their biological functions. In this R35 grant, we continue uncovering the simplicity and versatility of phenanthroline catalysts to provide a new principle for the stereoselective construction of the challenging α-2-deoxy glycosides. Precisely tailored phenanthroline catalysts can activate both the alcohol nucleophile and the glycosyl halide electrophile simultaneously. We will also investigate the dual activation mechanism of the phenanthroline catalysts to control site- selective coupling of polyol nucleophiles and chemoselective coupling of the hydroxyl of serine residue in the presence of the thiol of cysteine-containing peptides. Further, we will apply the phenanthroline catalyst platform to the synthesis of heparan sulfate-like oligosaccharides as inhibitors of heparanase, which is a druggable target for anticancer therapy. We will also develop the library of heparan sulfate mimetics with all of the possible O- and N-sulfation motifs from readily available aminoglycosides to advance an understanding of the role of sulfated glycosaminoglycans in many biological systems. In particular, we will investigate these structurally well-defined heparan sulfate mimetics as the potential binders of clinically important fibroblast growth factors.


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 = $524,144 )
2025	2025	WAYNE STATE UNIVERSITY	5700 CASS AVE STE 4900	DETROIT	MI	48202	WAYNE	USA	Biomedical Research and Research Training	001	3	7/29/2025	NON-COMPETING CONTINUATION	$524,144
2025	2024	WAYNE STATE UNIVERSITY	5700 CASS AVE STE 4900	DETROIT	MI	48202	WAYNE	USA	Biomedical Research and Research Training	000	2	11/5/2024	NON-COMPETING CONTINUATION	$0
														Subtotal = $524,144

Issue Date FY: 2024 ( Subtotal = $524,144 )
2024	2024	WAYNE STATE UNIVERSITY	5700 CASS AVE STE 4900	DETROIT	MI	48202	WAYNE	USA	Biomedical Research and Research Training	000	2	8/28/2024	NON-COMPETING CONTINUATION	$524,144
														Subtotal = $524,144

Issue Date FY: 2023 ( Subtotal = $325,842 )
2023	2023	WAYNE STATE UNIVERSITY	5700 CASS AVE STE 4900	DETROIT	MI	48202	WAYNE	USA	Biomedical Research and Research Training	000	1	8/22/2023	NEW	$325,842
														Subtotal = $325,842

Grand Total All Awards = $1,374,130

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Development of Catalytic Glycosylations and Biologically Important Glycosaminoglycans

Award Number: R35GM149213

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: 09/01/2023

PERIOD OF PERFORMANCE END DATE: 08/31/2028

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