YbtT is a low-specificity type II thioesterase that maintains production of the metallophore yersiniabactin in pathogenic enterobacteria

Ohlemacher, Shannon I.; Xu, Yiquan; Kober, Daniel L.; Malik, Mahnoor; Nix, Jay C.; Brett, Tom J.; Henderson, Jeffrey P.

doi:10.1074/jbc.RA118.005752

Title: YbtT is a low-specificity type II thioesterase that maintains production of the metallophore yersiniabactin in pathogenic enterobacteria

Journal Article · 01 December 2018 · Journal of Biological Chemistry

DOI: https://doi.org/10.1074/jbc.RA118.005752 · OSTI ID:1769472

Ohlemacher, Shannon I.; Xu, Yiquan; Kober, Daniel L.; Malik, Mahnoor; Nix, Jay C.; Brett, Tom J.; Henderson, Jeffrey P.

Not Available

View Journal Article

Cite

Export

Save

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1769472

Journal Information:: Journal of Biological Chemistry, Journal Name: Journal of Biological Chemistry Journal Issue: 51 Vol. 293; ISSN 0021-9258

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (57)

Evidence that a Novel Thioesterase is Responsible for Polyketide Chain Release during Biosynthesis of the Polyether Ionophore Monensin Harvey, Barbara M.; Hong, Hui; Jones, Michelle A. ChemBioChem, Vol. 7, Issue 9 https://doi.org/10.1002/cbic.200500474	journal	August 2006
The Thioesterase Bhp is Involved in the Formation of β-Hydroxytyrosine during Balhimycin Biosynthesis in Amycolatopsis balhimycina Mulyani, Sri; Egel, Ellen; Kittel, Claudia ChemBioChem, Vol. 11, Issue 2 https://doi.org/10.1002/cbic.200900600	journal	January 2010
Roles of type II thioesterases and their application for secondary metabolite yield improvement Kotowska, Magdalena; Pawlik, Krzysztof Applied Microbiology and Biotechnology, Vol. 98, Issue 18 https://doi.org/10.1007/s00253-014-5952-8	journal	August 2014
New proteolytic enzymes in yeast Achstetter, Tilman; Ehmann, Claudia; Wolf, Dieter H. Archives of Biochemistry and Biophysics, Vol. 207, Issue 2 https://doi.org/10.1016/0003-9861(81)90052-7	journal	April 1981
Structural Basis for the Cyclization of the Lipopeptide Antibiotic Surfactin by the Thioesterase Domain SrfTE Bruner, Steven D.; Weber, Thomas; Kohli, Rahul M. Structure, Vol. 10, Issue 3 https://doi.org/10.1016/S0969-2126(02)00716-5	journal	March 2002
Role of type II thioesterases: evidence for removal of short acyl chains produced by aberrant decarboxylation of chain extender units Heathcote, Michelle L.; Staunton, James; Leadlay, Peter F. Chemistry & Biology, Vol. 8, Issue 2, p. 207-220 https://doi.org/10.1016/S1074-5521(01)00002-3	journal	February 2001
Yersiniabactin Synthetase Miller, Deborah Ann; Luo, Lusong; Hillson, Nathan Chemistry & Biology, Vol. 9, Issue 3 https://doi.org/10.1016/S1074-5521(02)00115-1	journal	March 2002
Impact of thioesterase activity on tylosin biosynthesis in Streptomyces fradiae Butler, Andrew R.; Bate, Neil; Cundliffe, Eric Chemistry & Biology, Vol. 6, Issue 5 https://doi.org/10.1016/S1074-5521(99)80074-X	journal	May 1999
Top-down mass spectrometry on low-resolution instruments: Characterization of phosphopantetheinylated carrier domains in polyketide and non-ribosomal biosynthetic pathways Meluzzi, Dario; Zheng, Wei Hao; Hensler, Mary Bioorganic & Medicinal Chemistry Letters, Vol. 18, Issue 10 https://doi.org/10.1016/j.bmcl.2007.10.104	journal	May 2008
Identification of NanE as the Thioesterase for Polyether Chain Release in Nanchangmycin Biosynthesis Liu, Tiangang; You, Delin; Valenzano, Chiara Chemistry & Biology, Vol. 13, Issue 9 https://doi.org/10.1016/j.chembiol.2006.07.006	journal	September 2006
Yersiniabactin iron uptake: mechanisms and role in Yersinia pestis pathogenesis Perry, Robert D.; Fetherston, Jacqueline D. Microbes and Infection, Vol. 13, Issue 10 https://doi.org/10.1016/j.micinf.2011.04.008	journal	September 2011
Structure and Functional Analysis of ClbQ, an Unusual Intermediate-Releasing Thioesterase from the Colibactin Biosynthetic Pathway Guntaka, Naga Sandhya; Healy, Alan R.; Crawford, Jason M. ACS Chemical Biology, Vol. 12, Issue 10 https://doi.org/10.1021/acschembio.7b00479	journal	September 2017
Facile Detection of Acyl and Peptidyl Intermediates on Thiotemplate Carrier Domains via Phosphopantetheinyl Elimination Reactions during Tandem Mass Spectrometry ^† Dorrestein, Pieter C.; Bumpus, Stefanie B.; Calderone, Christopher T. Biochemistry, Vol. 45, Issue 42 https://doi.org/10.1021/bi061169d	journal	October 2006
Two Structures of a Thiazolinyl Imine Reductase from Yersinia enterocolitica Provide Insight into Catalysis and Binding to the Nonribosomal Peptide Synthetase Module of HMWP1 Meneely, Kathleen M.; Lamb, Audrey L. Biochemistry, Vol. 51, Issue 44 https://doi.org/10.1021/bi3011016	journal	October 2012
In Vitro Kinetic Analysis of Substrate Specificity in Enterobactin Biosynthetic Lower Pathway Enzymes Provides Insight into the Biochemical Function of the Hot Dog-Fold Thioesterase EntH ^† Chen, Danqi; Wu, Rui; Bryan, Tyrel L. Biochemistry, Vol. 48, Issue 3 https://doi.org/10.1021/bi802207t	journal	January 2009
Characterization of Sfp, a Bacillus subtilis Phosphopantetheinyl Transferase for Peptidyl Carrier Protein Domains in Peptide Synthetases ^† Quadri, Luis E. N.; Weinreb, Paul H.; Lei, Ming Biochemistry, Vol. 37, Issue 6 https://doi.org/10.1021/bi9719861	journal	February 1998
The Nonribosomal Peptide Synthetase HMWP2 Forms a Thiazoline Ring during Biogenesis of Yersiniabactin, an Iron-Chelating Virulence Factor of Yersinia p estis ^† Gehring, Amy M.; Mori, Ichiro; Perry, Robert D. Biochemistry, Vol. 37, Issue 33 https://doi.org/10.1021/bi9812571	journal	August 1998
Expression, Purification, and Characterization of HMWP2, a 229 kDa, Six Domain Protein Subunit of Yersiniabactin Synthetase ^† Keating, Thomas A.; Miller, Deborah Ann; Walsh, Christopher T. Biochemistry, Vol. 39, Issue 16 https://doi.org/10.1021/bi992923g	journal	April 2000
Yersinia High Pathogenicity Island Genes Modify the Escherichia coli Primary Metabolome Independently of Siderophore Production Lv, Haitao; Henderson, Jeffrey P. Journal of Proteome Research, Vol. 10, Issue 12 https://doi.org/10.1021/pr200756n	journal	December 2011
Structural basis for the selectivity of the external thioesterase of the surfactin synthetase Koglin, Alexander; Löhr, Frank; Bernhard, Frank Nature, Vol. 454, Issue 7206 https://doi.org/10.1038/nature07161	journal	August 2008
Dynamic thiolation–thioesterase structure of a non-ribosomal peptide synthetase Frueh, Dominique P.; Arthanari, Haribabu; Koglin, Alexander Nature, Vol. 454, Issue 7206 https://doi.org/10.1038/nature07162	journal	August 2008
Structures of two distinct conformations of holo-non-ribosomal peptide synthetases Drake, Eric J.; Miller, Bradley R.; Shi, Ce Nature, Vol. 529, Issue 7585 https://doi.org/10.1038/nature16163	journal	January 2016
The siderophore yersiniabactin binds copper to protect pathogens during infection Chaturvedi, Kaveri S.; Hung, Chia S.; Crowley, Jan R. Nature Chemical Biology, Vol. 8, Issue 8 https://doi.org/10.1038/nchembio.1020	journal	July 2012
Copper import in Escherichia coli by the yersiniabactin metallophore system Koh, Eun-Ik; Robinson, Anne E.; Bandara, Nilantha Nature Chemical Biology, Vol. 13, Issue 9 https://doi.org/10.1038/nchembio.2441	journal	July 2017
Data publication with the structural biology data grid supports live analysis Meyer, Peter A.; Socias, Stephanie; Key, Jason Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms10882	journal	March 2016
Site-specific protein labeling by Sfp phosphopantetheinyl transferase Yin, Jun; Lin, Alison J.; Golan, David E. Nature Protocols, Vol. 1, Issue 1 https://doi.org/10.1038/nprot.2006.43	journal	June 2006
The chemical biology of modular biosynthetic enzymes Meier, Jordan L.; Burkart, Michael D. Chemical Society Reviews, Vol. 38, Issue 7 https://doi.org/10.1039/b805115c	journal	January 2009
Characterization of TioQ, a type II thioesterase from the thiocoraline biosynthetic cluster Mady, Ahmed S. A.; Zolova, Olga E.; Millán, María Álvarez San Molecular BioSystems, Vol. 7, Issue 6 https://doi.org/10.1039/c1mb05044c	journal	January 2011
Identification of genes subject to positive selection in uropathogenic strains of Escherichia coli: A comparative genomics approach Chen, S. L.; Hung, C. -S.; Xu, J. Proceedings of the National Academy of Sciences, Vol. 103, Issue 15 https://doi.org/10.1073/pnas.0600938103	journal	April 2006
One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products Datsenko, K. A.; Wanner, B. L. Proceedings of the National Academy of Sciences, Vol. 97, Issue 12, p. 6640-6645 https://doi.org/10.1073/pnas.120163297	journal	May 2000
Regeneration of misprimed nonribosomal peptide synthetases by type II thioesterases Schwarzer, D.; Mootz, H. D.; Linne, U. Proceedings of the National Academy of Sciences, Vol. 99, Issue 22 https://doi.org/10.1073/pnas.212382199	journal	October 2002
Acyl-CoA hydrolysis by the high molecular weight protein 1 subunit of yersiniabactin synthetase: Mutational evidence for a cascade of four acyl-enzyme intermediates during hydrolytic editing Suo, Z.; Chen, H.; Walsh, C. T. Proceedings of the National Academy of Sciences, Vol. 97, Issue 26 https://doi.org/10.1073/pnas.260495697	journal	December 2000
Purification, priming, and catalytic acylation of carrier protein domains in the polyketide synthase and nonribosomal peptidyl synthetase modules of the HMWP1 subunit of yersiniabactin synthetase Suo, Z.; Tseng, C. C.; Walsh, C. T. Proceedings of the National Academy of Sciences, Vol. 98, Issue 1 https://doi.org/10.1073/pnas.98.1.99	journal	January 2001
Structure and Function of the RedJ Protein, a Thioesterase from the Prodiginine Biosynthetic Pathway in Streptomyces coelicolor Whicher, Jonathan R.; Florova, Galina; Sydor, Paulina K. Journal of Biological Chemistry, Vol. 286, Issue 25 https://doi.org/10.1074/jbc.M110.213512	journal	May 2011
Crystal Structure and Substrate Specificity of Human Thioesterase 2: INSIGHTS INTO THE MOLECULAR BASIS FOR THE MODULATION OF FATTY ACID SYNTHASE Ritchie, Melissa K.; Johnson, Lynnette C.; Clodfelter, Jill E. Journal of Biological Chemistry, Vol. 291, Issue 7 https://doi.org/10.1074/jbc.M115.702597	journal	December 2015
Structure and Functional Analysis of RifR, the Type II Thioesterase from the Rifamycin Biosynthetic Pathway Claxton, Heather B.; Akey, David L.; Silver, Monica K. Journal of Biological Chemistry, Vol. 284, Issue 8 https://doi.org/10.1074/jbc.M808604200	journal	December 2008
Uropathogenic enterobacteria use the yersiniabactin metallophore system to acquire nickel Robinson, Anne E.; Lowe, Jessica E.; Koh, Eun-Ik Journal of Biological Chemistry, Vol. 293, Issue 39 https://doi.org/10.1074/jbc.RA118.004483	journal	September 2018
CAVER Analyst 1.0: graphic tool for interactive visualization and analysis of tunnels and channels in protein structures Kozlikova, Barbora; Sebestova, Eva; Sustr, Vilem Bioinformatics, Vol. 30, Issue 18 https://doi.org/10.1093/bioinformatics/btu364	journal	May 2014
Dali server update Holm, Liisa; Laakso, Laura M. Nucleic Acids Research, Vol. 44, Issue W1 https://doi.org/10.1093/nar/gkw357	journal	April 2016
Reduced synthesis of the Ybt siderophore or production of aberrant Ybt-like molecules activates transcription of yersiniabactin genes in Yersinia pestis Miller, M. Clarke; Fetherston, Jacqueline D.; Pickett, Carol L. Microbiology, Vol. 156, Issue 7 https://doi.org/10.1099/mic.0.037945-0	journal	July 2010
Phaser crystallographic software McCoy, Airlie J.; Grosse-Kunstleve, Ralf W.; Adams, Paul D. Journal of Applied Crystallography, Vol. 40, Issue 4 https://doi.org/10.1107/S0021889807021206	journal	July 2007
PHENIX : building new software for automated crystallographic structure determination Adams, Paul D.; Grosse-Kunstleve, Ralf W.; Hung, Li-Wei Acta Crystallographica Section D Biological Crystallography, Vol. 58, Issue 11 https://doi.org/10.1107/S0907444902016657	journal	October 2002
Coot model-building tools for molecular graphics Emsley, Paul; Cowtan, Kevin Acta Crystallographica Section D Biological Crystallography, Vol. 60, Issue 12, p. 2126-2132 https://doi.org/10.1107/S0907444904019158	journal	November 2004
XDS Kabsch, Wolfgang Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2 https://doi.org/10.1107/S0907444909047337	journal	January 2010
Automated MAD and MIR structure solution Terwilliger, Thomas C.; Berendzen, Joel Acta Crystallographica Section D Biological Crystallography, Vol. 55, Issue 4 https://doi.org/10.1107/S0907444999000839	journal	April 1999
Type II Thioesterase ScoT, Associated with Streptomyces coelicolor A3(2) Modular Polyketide Synthase Cpk, Hydrolyzes Acyl Residues and Has a Preference for Propionate Kotowska, Magdalena; Pawlik, Krzysztof; Smulczyk-Krawczyszyn, Aleksandra Applied and Environmental Microbiology, Vol. 75, Issue 4 https://doi.org/10.1128/AEM.01371-08	journal	December 2008
Iron Homeostasis Regulates the Genotoxicity of Escherichia coli That Produces Colibactin Tronnet, Sophie; Garcie, Christophe; Rehm, Nadine Infection and Immunity, Vol. 84, Issue 12 https://doi.org/10.1128/IAI.00659-16	journal	September 2016
Yersinia pestis YbtU and YbtT Are Involved in Synthesis of the Siderophore Yersiniabactin but Have Different Effects on Regulation Geoffroy, Valerie A.; Fetherston, Jacqueline D.; Perry, Robert D. Infection and Immunity, Vol. 68, Issue 8 https://doi.org/10.1128/IAI.68.8.4452-4461.2000	journal	August 2000
Establishment of a Persistent Escherichia coli Reservoir during the Acute Phase of a Bladder Infection Mulvey, Matthew A.; Schilling, Joel D.; Hultgren, Scott J. Infection and Immunity, Vol. 69, Issue 7 https://doi.org/10.1128/IAI.69.7.4572-4579.2001	journal	July 2001
The Hotdog Thioesterase EntH (YbdB) Plays a Role In Vivo in Optimal Enterobactin Biosynthesis by Interacting with the ArCP Domain of EntB Leduc, Damien; Battesti, Aurélia; Bouveret, Emmanuelle Journal of Bacteriology, Vol. 189, Issue 19 https://doi.org/10.1128/JB.00755-07	journal	August 2007
PchC Thioesterase Optimizes Nonribosomal Biosynthesis of the Peptide Siderophore Pyochelin in Pseudomonas aeruginosa Reimmann, Cornelia; Patel, Hiten M.; Walsh, Christopher T. Journal of Bacteriology, Vol. 186, Issue 19 https://doi.org/10.1128/JB.186.19.6367-6373.2004	journal	October 2004
Genetics and Assembly Line Enzymology of Siderophore Biosynthesis in Bacteria Crosa, Jorge H.; Walsh, Christopher T. Microbiology and Molecular Biology Reviews, Vol. 66, Issue 2 https://doi.org/10.1128/MMBR.66.2.223-249.2002	journal	June 2002
Enterobacteria secrete an inhibitor of Pseudomonas virulence during clinical bacteriuria Ohlemacher, Shannon I.; Giblin, Daryl E.; d’Avignon, D. André Journal of Clinical Investigation, Vol. 127, Issue 11 https://doi.org/10.1172/JCI92464	journal	September 2017
CAVER 3.0: A Tool for the Analysis of Transport Pathways in Dynamic Protein Structures Chovancova, Eva; Pavelka, Antonin; Benes, Petr PLoS Computational Biology, Vol. 8, Issue 10 https://doi.org/10.1371/journal.pcbi.1002708	journal	October 2012
Quantitative Metabolomics Reveals an Epigenetic Blueprint for Iron Acquisition in Uropathogenic Escherichia coli Henderson, Jeffrey P.; Crowley, Jan R.; Pinkner, Jerome S. PLoS Pathogens, Vol. 5, Issue 2 https://doi.org/10.1371/journal.ppat.1000305	journal	February 2009
The iron hand of uropathogenic Escherichia coli : the role of transition metal control in virulence Robinson, Anne E.; Heffernan, James R.; Henderson, Jeffrey P. Future Microbiology, Vol. 13, Issue 7 https://doi.org/10.2217/fmb-2017-0295	journal	June 2018
Collaboration gets the most out of software Morin, Andrew; Eisenbraun, Ben; Key, Jason eLife, Vol. 2 https://doi.org/10.7554/eLife.01456	journal	September 2013

Similar Records

Structure and Function of BorB, the Type II Thioesterase from the Borrelidin Biosynthetic Gene Cluster

Journal Article · 2020 · Biochemistry · OSTI ID:1721637

Curran, Samuel C.; Pereira, Jose H.; Baluyot, Marian-Joy; +5 more

Identification of an unusual type II thioesterase in the dithiolopyrrolone antibiotics biosynthetic pathway

Journal Article · 2016 · Biochemical and Biophysical Research Communications · OSTI ID:22596352

Zhai, Ying; Bai, Silei; Liu, Jingjing; +4 more

Structure and Functional Analysis of RifR, the Type II Thioesterase from the Rifamycin Biosynthetic Pathway

Journal Article · 2009 · J. Biol. Chem. · OSTI ID:1005484

Claxton, Heather B; Akey, David L; Silver, Monica K; +2 more

Title: YbtT is a low-specificity type II thioesterase that maintains production of the metallophore yersiniabactin in pathogenic enterobacteria

Citation Formats

References (57)

Similar Records

Related Subjects