Enzymatic β-Oxidation of the Cholesterol Side Chain in Mycobacterium tuberculosis Bifurcates Stereospecifically at Hydration of 3-Oxo-cholest-4,22-dien-24-oyl-CoA

Yuan, T; Werman, J.; Yin, X.; Yang, M.; Garcia-Diaz, M.; Sampson, N.

doi:10.1021/acsinfecdis.1c00069

Enzymatic β-Oxidation of the Cholesterol Side Chain in Mycobacterium tuberculosis Bifurcates Stereospecifically at Hydration of 3-Oxo-cholest-4,22-dien-24-oyl-CoA

Journal Article · 01 January 2022 · ACS Infectious Diseases

DOI:https://doi.org/10.1021/acsinfecdis.1c00069· OSTI ID:1808965

Yuan, T; Werman, J.; Yin, X.; Yang, M.; Garcia-Diaz, M.; Sampson, N.

Research Organization:: Brookhaven National Lab. (BNL), Upton, NY (United States)

Sponsoring Organization:: ~OTHER

DOE Contract Number:: SC0012704

OSTI ID:: 1808965

Report Number(s):: BNL-221860-2021-JACI

Journal Information:: ACS Infectious Diseases, Vol. 7, Issue 6

Country of Publication:: United States

Language:: English

References (43)

The pursuit of mechanism of action: uncovering drug complexity in TB drug discovery Yuan, Tianao; Werman, Joshua M.; Sampson, Nicole S. RSC Chemical Biology, Vol. 2, Issue 2 https://doi.org/10.1039/D0CB00226G	journal	January 2021
Metabolomics of Mycobacterium tuberculosis Reveals Compartmentalized Co-Catabolism of Carbon Substrates de Carvalho, Luiz Pedro S.; Fischer, Steven M.; Marrero, Joeli Chemistry & Biology, Vol. 17, Issue 10 https://doi.org/10.1016/j.chembiol.2010.08.009	journal	October 2010
Mycobacterial persistence requires the utilization of host cholesterol Pandey, A. K.; Sassetti, C. M. Proceedings of the National Academy of Sciences, Vol. 105, Issue 11 https://doi.org/10.1073/pnas.0711159105	journal	March 2008
Cholesterol and fatty acids grease the wheels of Mycobacterium tuberculosis pathogenesis Wilburn, Kaley M.; Fieweger, Rachael A.; VanderVen, Brian C. Pathogens and Disease, Vol. 76, Issue 2 https://doi.org/10.1093/femspd/fty021	journal	March 2018
Hit Generation in TB Drug Discovery: From Genome to Granuloma Yuan, Tianao; Sampson, Nicole S. Chemical Reviews, Vol. 118, Issue 4 https://doi.org/10.1021/acs.chemrev.7b00602	journal	January 2018
More than cholesterol catabolism: regulatory vulnerabilities in Mycobacterium tuberculosis Bonds, Amber C.; Sampson, Nicole S. Current Opinion in Chemical Biology, Vol. 44 https://doi.org/10.1016/j.cbpa.2018.05.012	journal	June 2018
Novel Inhibitors of Cholesterol Degradation in Mycobacterium tuberculosis Reveal How the Bacterium’s Metabolism Is Constrained by the Intracellular Environment VanderVen, Brian C.; Fahey, Ruth J.; Lee, Wonsik PLOS Pathogens, Vol. 11, Issue 2 https://doi.org/10.1371/journal.ppat.1004679	journal	February 2015
Mce3R Stress-Resistance Pathway Is Vulnerable to Small-Molecule Targeting That Improves Tuberculosis Drug Activities Yang, Xinxin; Yuan, Tianao; Ma, Rui ACS Infectious Diseases, Vol. 5, Issue 7 https://doi.org/10.1021/acsinfecdis.9b00099	journal	April 2019
Pathogen roid rage: Cholesterol utilization by Mycobacterium tuberculosis Wipperman, Matthew F.; Sampson, Nicole S.; Thomas, Suzanne T. Critical Reviews in Biochemistry and Molecular Biology, Vol. 49, Issue 4 https://doi.org/10.3109/10409238.2014.895700	journal	March 2014
Role of the methylcitrate cycle in propionate metabolism and detoxification in Mycobacterium smegmatis Upton, A. M.; McKinney, J. D. Microbiology, Vol. 153, Issue 12 https://doi.org/10.1099/mic.0.2007/011726-0	journal	December 2007
Functional Characterization of a Vitamin B12-Dependent Methylmalonyl Pathway in Mycobacterium tuberculosis: Implications for Propionate Metabolism during Growth on Fatty Acids Savvi, S.; Warner, D. F.; Kana, B. D. Journal of Bacteriology, Vol. 190, Issue 11 https://doi.org/10.1128/JB.01767-07	journal	March 2008
Intracellular Mycobacterium tuberculosis Exploits Host-derived Fatty Acids to Limit Metabolic Stress Lee, Wonsik; VanderVen, Brian C.; Fahey, Ruth J. Journal of Biological Chemistry, Vol. 288, Issue 10 https://doi.org/10.1074/jbc.M112.445056	journal	January 2013
A Thiolase of Mycobacterium tuberculosis Is Required for Virulence and Production of Androstenedione and Androstadienedione from Cholesterol Nesbitt, Natasha M.; Yang, Xinxin; Fontán, Patricia Infection and Immunity, Vol. 78, Issue 1 https://doi.org/10.1128/IAI.00893-09	journal	January 2010
Identification and Characterization of a New Enoyl Coenzyme A Hydratase Involved in Biosynthesis of Medium-Chain-Length Polyhydroxyalkanoates in Recombinant Escherichia coli Park, Si Jae; Lee, Sang Yup Journal of Bacteriology, Vol. 185, Issue 18 https://doi.org/10.1128/JB.185.18.5391-5397.2003	journal	September 2003
Post-translational Succinylation of Mycobacterium tuberculosis Enoyl-CoA Hydratase EchA19 Slows Catalytic Hydration of Cholesterol Catabolite 3-Oxo-chol-4,22-diene-24-oyl-CoA Bonds, Amber C.; Yuan, Tianao; Werman, Joshua M. ACS Infectious Diseases, Vol. 6, Issue 8 https://doi.org/10.1021/acsinfecdis.0c00329	journal	July 2020
Binary Structure of the Two-Domain (3R)-Hydroxyacyl-CoA Dehydrogenase from Rat Peroxisomal Multifunctional Enzyme Type 2 at 2.38 Å Resolution Haapalainen, Antti M.; Koski, M. Kristian; Qin, Yong-Mei Structure, Vol. 11, Issue 1 https://doi.org/10.1016/S0969-2126(02)00931-0	journal	January 2003
Crystal Structure of Yeast Peroxisomal Multifunctional Enzyme: Structural Basis for Substrate Specificity of (3R)-hydroxyacyl-CoA Dehydrogenase Units Ylianttila, Mari S.; Pursiainen, Niko V.; Haapalainen, Antti M. Journal of Molecular Biology, Vol. 358, Issue 5 https://doi.org/10.1016/j.jmb.2006.03.001	journal	May 2006
The catalytic reaction and inhibition mechanism of Drosophila alcohol dehydrogenase: observation of an enzyme-bound NAD-ketone adduct at 1.4 Å resolution by X-ray crystallography Benach, Jordi; Atrian, Sı́lvia; Gonzàlez-Duarte, Roser Journal of Molecular Biology, Vol. 289, Issue 2 https://doi.org/10.1006/jmbi.1999.2765	journal	June 1999
Automatic generation of protein structure cartoons with Pro-origami Stivala, A.; Wybrow, M.; Wirth, A. Bioinformatics, Vol. 27, Issue 23 https://doi.org/10.1093/bioinformatics/btr575	journal	October 2011
Chemical and biological evolution of a nucleotide-binding protein Rossmann, Michael G.; Moras, Dino; Olsen, Kenneth W. Nature, Vol. 250, Issue 5463 https://doi.org/10.1038/250194a0	journal	July 1974
CoABind: a novel algorithm for Coenzyme A (CoA)- and CoA derivatives-binding residues prediction Meng, Qiaozhen; Peng, Zhenling; Yang, Jianyi Bioinformatics, Vol. 34, Issue 15 https://doi.org/10.1093/bioinformatics/bty162	journal	March 2018
Structural and Biochemical Characterization of Mycobacterium tuberculosis CYP142 Driscoll, Max D.; McLean, Kirsty J.; Levy, Colin Journal of Biological Chemistry, Vol. 285, Issue 49 https://doi.org/10.1074/jbc.M110.164293	journal	December 2010
Unraveling Cholesterol Catabolism in Mycobacterium tuberculosis : ChsE4-ChsE5 α ₂ β ₂ Acyl-CoA Dehydrogenase Initiates β-Oxidation of 3-Oxo-cholest-4-en-26-oyl CoA Yang, Meng; Lu, Rui; Guja, Kip E. ACS Infectious Diseases, Vol. 1, Issue 2 https://doi.org/10.1021/id500033m	journal	January 2015
α-Methyl Acyl CoA Racemase Provides Mycobacterium tuberculosis Catabolic Access to Cholesterol Esters Lu, Rui; Schmitz, Werner; Sampson, Nicole S. Biochemistry, Vol. 54, Issue 37 https://doi.org/10.1021/acs.biochem.5b00911	journal	September 2015
FadA5 a Thiolase from Mycobacterium tuberculosis : A Steroid-Binding Pocket Reveals the Potential for Drug Development against Tuberculosis Schaefer, Christin M.; Lu, Rui; Nesbitt, Natasha M. Structure, Vol. 23, Issue 1 https://doi.org/10.1016/j.str.2014.10.010	journal	January 2015
Unraveling and engineering the production of 23,24-bisnorcholenic steroids in sterol metabolism Xu, Li-Qin; Liu, Yong-Jun; Yao, Kang Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep21928	journal	February 2016
Mycobacterium tuberculosis Exploits a Heterohexameric Enoyl-CoA Hydratase Retro-Aldolase Complex for Cholesterol Catabolism Yuan, Tianao; Yang, Meng; Gehring, Kalle Biochemistry, Vol. 58, Issue 41 https://doi.org/10.1021/acs.biochem.9b00673	journal	September 2019
Characterization of an Aldolase Involved in Cholesterol Side Chain Degradation in Mycobacterium tuberculosis Gilbert, Stephanie; Hood, LaChae; Seah, Stephen Y. K. Journal of Bacteriology, Vol. 200, Issue 2 https://doi.org/10.1128/JB.00512-17	journal	January 2018
The Essential Function of Genes for a Hydratase and an Aldehyde Dehydrogenase for Growth of Pseudomonas sp. Strain Chol1 with the Steroid Compound Cholate Indicates an Aldolytic Reaction Step for Deacetylation of the Side Chain Holert, Johannes; Jagmann, Nina; Philipp, Bodo Journal of Bacteriology, Vol. 195, Issue 15 https://doi.org/10.1128/JB.00410-13	journal	August 2013
A patchwork pathway for oxygenase-independent degradation of side chain containing steroids: Anaerobic degradation of steroids Warnke, Markus; Jacoby, Christian; Jung, Tobias Environmental Microbiology, Vol. 19, Issue 11 https://doi.org/10.1111/1462-2920.13933	journal	November 2017
Functional Characterization of Three Specific Acyl-Coenzyme A Synthetases Involved in Anaerobic Cholesterol Degradation in Sterolibacterium denitrificans Chol1S Warnke, Markus; Jung, Tobias; Jacoby, Christian Applied and Environmental Microbiology, Vol. 84, Issue 7 https://doi.org/10.1128/AEM.02721-17	journal	April 2018
High-Resolution Phenotypic Profiling Defines Genes Essential for Mycobacterial Growth and Cholesterol Catabolism Griffin, Jennifer E.; Gawronski, Jeffrey D.; DeJesus, Michael A. PLoS Pathogens, Vol. 7, Issue 9 https://doi.org/10.1371/journal.ppat.1002251	journal	September 2011
Genetic requirements for mycobacterial survival during infection Sassetti, C. M.; Rubin, E. J. Proceedings of the National Academy of Sciences, Vol. 100, Issue 22 https://doi.org/10.1073/pnas.2134250100	journal	October 2003
A gene cluster encoding cholesterol catabolism in a soil actinomycete provides insight into Mycobacterium tuberculosis survival in macrophages Van der Geize, R.; Yam, K.; Heuser, T. Proceedings of the National Academy of Sciences, Vol. 104, Issue 6 https://doi.org/10.1073/pnas.0605728104	journal	January 2007
Intermembrane transfer of 5 alpha-cholest-7-en-3 beta-ol. Facilitation by supernatant protein (SCP). Ishibashi, T.; Bloch, K. Journal of Biological Chemistry, Vol. 256, Issue 24 https://doi.org/10.1016/S0021-9258(18)42990-0	journal	December 1981
Sterol carrier protein X is peroxisomal 3-oxoacyl coenzyme A thiolase with intrinsic sterol carrier and lipid transfer activity. Seedorf, U.; Brysch, P.; Engel, T. Journal of Biological Chemistry, Vol. 269, Issue 33 https://doi.org/10.1016/S0021-9258(17)31960-9	journal	August 1994
Mycobacterium tuberculosis Utilizes a Unique Heterotetrameric Structure for Dehydrogenation of the Cholesterol Side Chain Thomas, Suzanne T.; Sampson, Nicole S. Biochemistry, Vol. 52, Issue 17 https://doi.org/10.1021/bi4002979	journal	April 2013
Shrinking the FadE Proteome of Mycobacterium tuberculosis: Insights into Cholesterol Metabolism through Identification of an α ₂ β ₂ Heterotetrameric Acyl Coenzyme A Dehydrogenase Family Wipperman, Matthew F.; Yang, Meng; Thomas, Suzanne T. Journal of Bacteriology, Vol. 195, Issue 19 https://doi.org/10.1128/JB.00502-13	journal	October 2013
A Distinct MaoC-like Enoyl-CoA Hydratase Architecture Mediates Cholesterol Catabolism in Mycobacterium tuberculosis Yang, Meng; Guja, Kip E.; Thomas, Suzanne T. ACS Chemical Biology, Vol. 9, Issue 11 https://doi.org/10.1021/cb500232h	journal	September 2014
IpdE1-IpdE2 Is a Heterotetrameric Acyl Coenzyme A Dehydrogenase That Is Widely Distributed in Steroid-Degrading Bacteria Gadbery, John E.; Round, James W.; Yuan, Tianao Biochemistry, Vol. 59, Issue 10 https://doi.org/10.1021/acs.biochem.0c00005	journal	February 2020
XDS Kabsch, Wolfgang Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2 https://doi.org/10.1107/S0907444909047337	journal	January 2010
How good are my data and what is the resolution? Evans, Philip R.; Murshudov, Garib N. Acta Crystallographica Section D Biological Crystallography, Vol. 69, Issue 7 https://doi.org/10.1107/S0907444913000061	journal	June 2013
Data processing and analysis with the autoPROC toolbox Vonrhein, Clemens; Flensburg, Claus; Keller, Peter Acta Crystallographica Section D Biological Crystallography, Vol. 67, Issue 4 https://doi.org/10.1107/S0907444911007773	journal	March 2011

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