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Polyketides via Redox-Triggered Alcohol C-H Functionalization

Award Number: R01GM093905
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: 05/01/2011
PERIOD OF PERFORMANCE END DATE: 05/31/2025

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Polyketides via Redox-Triggered Alcohol C-H Functionalization - Polyketides are used more frequently in human medicine than any other class of secondary metabolites, and comprise roughly 20% of top-selling small-molecule drugs. Despite their importance: (a) All polyketides used in human medicine are derived from soil bacteria and are prepared via fermentation or semi-synthesis (notwithstanding eribulin), (b) <5% of soil bacteria are amenable to culture, many phyla have eluded culture, and the few bacteria amenable to culture express <10% of their biosynthetic genes, (c) although marine polyketides possess an astonishing array of biological activities, commercial fermentation processes involving marine bacteria (which are often symbionts) remain exceptionally uncommon. De novo chemical synthesis potentially offers entry to otherwise inaccessible polyketides and their congeners, yet current synthetic methods often do not avail sufficiently concise routes for large scale production. To overcome this challenge, our laboratory has pioneered a broad, new family of catalytic methods for the direct stereo- and site-selective conversion of lower alcohols to higher alcohols. As documented in numerous total syntheses, these methods streamline polyketide construction, allowing the target compounds to be prepared in significantly fewer steps than previously possible. In the proposed funding period, 3 specific aims are proposed: (a) Total syntheses of the type I polyketides neaumycin B and gladiolin will be pursued using our catalytic methods. Neaumycin B is a femtomolar inhibitor of U87 human glioblastoma. Gladiolin displays potent, selective activity against M. tuberculosis strains that are resistant to the frontline antibiotics isoniazid and rifampicin. (b) The type II polyketide antibiotics formicamycins G, H and J, arenimycin A and analogues of viridicatumtoxin will be prepared using our catalytic methods. Antibacterial properties of these compounds will be evaluated in collaboration with Prof. Barrie Wilkinson and Prof. Jean Chmielewski. (c) Ruthenium-catalyzed reactions relevant to polyketide construction (allylation, crotylation, propargylation, etc.) will be developed. Optimization of these methods will be assisted by computational studies performed by Prof. Kuo-Wei Huang. Thus, our studies advance an integrated program in which methodological innovation informs synthesis, and synthesis informs medicinal chemistry.


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 = -$33 )
2025	2024	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	002	14	1/31/2025	SUPPLEMENT FOR EXPANSION	$0
2025	2024	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	001	14	1/31/2025	NON-COMPETING CONTINUATION	$0
2025	2022	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	000	12	1/13/2025	NON-COMPETING CONTINUATION	-$33
														Subtotal = -$33

Issue Date FY: 2024 ( Subtotal = $439,114 )
2024	2024	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	005	14	5/10/2024	SUPPLEMENT FOR EXPANSION	$80,515
2024	2024	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	004	14	5/8/2024	NON-COMPETING CONTINUATION	$318,423
2024	2024	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	003	13	12/29/2023	SUPPLEMENT FOR EXPANSION	$40,176
2024	2023	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	001	13	12/5/2023	COMPETING CONTINUATION	$50,956
2024	2022	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	002	12	12/5/2023	SUPPLEMENT FOR EXPANSION	-$6,067
2024	2022	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	000	12	12/5/2023	NON-COMPETING CONTINUATION	-$44,889
														Subtotal = $439,114

Issue Date FY: 2023 ( Subtotal = $309,910 )
2023	2023	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	000	13	4/17/2023	COMPETING CONTINUATION	$309,910
														Subtotal = $309,910

Issue Date FY: 2022 ( Subtotal = $353,178 )
2022	2022	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	000	12	5/17/2022	NON-COMPETING CONTINUATION	$311,125
2022	2022	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	001	12	5/18/2022	SUPPLEMENT FOR EXPANSION	$42,053
														Subtotal = $353,178

Issue Date FY: 2021 ( Subtotal = $413,252 )
2021	2021	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	001	11	4/16/2021	NON-COMPETING CONTINUATION	$383,215
2021	2021	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	000	10	11/20/2020	SUPPLEMENT FOR EXPANSION	$30,037
														Subtotal = $413,252

Issue Date FY: 2020 ( Subtotal = $311,125 )
2020	2020	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	002	10	5/1/2020	NON-COMPETING CONTINUATION	$311,125
2020	2019	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	001	9	4/7/2020	COMPETING CONTINUATION	$125,275
2020	2018	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	000	8	4/7/2020	NON-COMPETING CONTINUATION	-$125,275
														Subtotal = $311,125

Issue Date FY: 2019 ( Subtotal = $287,960 )
2019	2019	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR, MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	000	9	4/19/2019	COMPETING CONTINUATION	$287,960
														Subtotal = $287,960

Issue Date FY: 2018 ( Subtotal = $287,547 )
2018	2018	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR, MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	000	8	5/21/2018	NON-COMPETING CONTINUATION	$287,547
														Subtotal = $287,547

Issue Date FY: 2017 ( Subtotal = $287,547 )
2017	2017	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR, MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	002	7	5/16/2017	NON-COMPETING CONTINUATION	$258,792
2017	2017	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR, MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	003	7	8/14/2017	NON-COMPETING CONTINUATION	$28,755
2017	2015	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR, MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	001	5	5/5/2017	COMPETING CONTINUATION	$2,520
2017	2014	UNIVERSITY OF TEXAS AT AUSTIN	110 INNER CAMPUS DR, MN 13	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	000	4	5/5/2017	NON-COMPETING CONTINUATION	-$2,520
														Subtotal = $287,547

Issue Date FY: 2016 ( Subtotal = $286,933 )
2016	2016	UNIVERSITY OF TEXAS AT AUSTIN	P.O. BOX 7159	AUSTIN	TX	78713	TRAVIS	USA	Biomedical Research and Research Training	000	6	6/1/2016	NON-COMPETING CONTINUATION	$286,933
														Subtotal = $286,933

Issue Date FY: 2015 ( Subtotal = $285,090 )
2015	2015	UNIVERSITY OF TEXAS AT AUSTIN	P.O. BOX 7159	AUSTIN	TX	78713	TRAVIS	USA	Biomedical Research and Research Training	001	5	6/12/2015	COMPETING CONTINUATION	$285,090
2015	2014	UNIVERSITY OF TEXAS AT AUSTIN	101 EAST 27TH STREET	AUSTIN	TX	78712	TRAVIS	USA	Biomedical Research and Research Training	000	4	6/9/2015	NON-COMPETING CONTINUATION	$0
														Subtotal = $285,090

Issue Date FY: 2014 ( Subtotal = $280,319 )
2014	2014	UNIVERSITY OF TEXAS AT AUSTIN	P.O. BOX 7159	AUSTIN	TX	78713	TRAVIS	USA	Biomedical Research and Research Training	000	4	4/18/2014	NON-COMPETING CONTINUATION	$280,319
														Subtotal = $280,319

Issue Date FY: 2013 ( Subtotal = $277,574 )
2013	2013	UNIVERSITY OF TEXAS AT AUSTIN	P.O. BOX 7159	AUSTIN	TX	78713	TRAVIS	USA	Biomedical Research and Research Training	001	3	6/14/2013	NON-COMPETING CONTINUATION	$18,697
2013	2013	UNIVERSITY OF TEXAS AT AUSTIN	P.O. BOX 7159	AUSTIN	TX	78713	TRAVIS	USA	Biomedical Research and Research Training	000	3	4/11/2013	NON-COMPETING CONTINUATION	$258,877
														Subtotal = $277,574

Issue Date FY: 2012 ( Subtotal = $352,151 )
2012	2012	UNIVERSITY OF TEXAS AT AUSTIN	P.O. BOX 7159	AUSTIN	TX	78713	TRAVIS	USA	Biomedical Research and Research Training	000	2	4/3/2012	NON-COMPETING CONTINUATION	$281,765
2012	2012	UNIVERSITY OF TEXAS AT AUSTIN	P.O. BOX 7159	AUSTIN	TX	78713	TRAVIS	USA	Biomedical Research and Research Training	001	2	5/10/2012	SUPPLEMENT FOR EXPANSION	$70,386
														Subtotal = $352,151

Issue Date FY: 2011 ( Subtotal = $282,464 )
2011	2011	UNIVERSITY OF TEXAS AT AUSTIN	P.O. BOX 7159	AUSTIN	TX	78713	TRAVIS	USA	Biomedical Research and Research Training	000	1	4/19/2011	NEW	$282,464
														Subtotal = $282,464

Grand Total All Awards = $4,454,131

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Polyketides via Redox-Triggered Alcohol C-H Functionalization

Award Number: R01GM093905

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: 05/01/2011

PERIOD OF PERFORMANCE END DATE: 05/31/2025

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