Structural Basis for Cyclopropanation by a Unique Enoyl-Acyl Carrier Protein Reductase

Khare, Dheeraj; Hale, Wendi A.; Tripathi, Ashootosh; Gu, Liangcai; Sherman, David H.; Gerwick, William H.; Håkansson, Kristina; Smith, Janet L.

doi:10.1016/j.str.2015.09.013

Title: Structural Basis for Cyclopropanation by a Unique Enoyl-Acyl Carrier Protein Reductase

Journal Article · Tue Dec 01 00:00:00 EST 2015 · Structure

DOI:https://doi.org/10.1016/j.str.2015.09.013· OSTI ID:1334209

Khare, Dheeraj; Hale, Wendi A.; Tripathi, Ashootosh; Gu, Liangcai; Sherman, David H.; Gerwick, William H.; Håkansson, Kristina; Smith, Janet L.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC); National Institutes of Health (NIH); NIH National Institute of General Medical Sciences (GM); National Cancer Institute (CA)

Grant/Contract Number:: DK-042303; CA-108874; GM107148

OSTI ID:: 1334209

Alternate ID(s):: OSTI ID: 1250910; OSTI ID: 1252755

Journal Information:: Structure, Journal Name: Structure Vol. 23 Journal Issue: 12; ISSN 0969-2126

Publisher:: ElsevierCopyright Statement

Country of Publication:: United Kingdom

Language:: English

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Cited by: 25 works

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References (48)

Biosynthesis of Radiolabeled Curacin A and Its Rapid and Apparently Irreversible Binding to the Colchicine Site of Tubulin Verdier-Pinard, Pascal; Sitachitta, Namthip; Rossi, James V. Archives of Biochemistry and Biophysics, Vol. 370, Issue 1 https://doi.org/10.1006/abbi.1999.1363	journal	October 1999
Isoprenoid-like alkylations in polyketide biosynthesis Calderone, Christopher T. Natural Product Reports, Vol. 25, Issue 5 https://doi.org/10.1039/b807243d	journal	January 2008
Divergence of multimodular polyketide synthases revealed by a didomain structure Zheng, Jianting; Gay, Darren C.; Demeler, Borries Nature Chemical Biology, Vol. 8, Issue 7 https://doi.org/10.1038/nchembio.964	journal	May 2012
Refinement of Macromolecular Structures by the Maximum-Likelihood Method Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallographica Section D Biological Crystallography, Vol. 53, Issue 3 https://doi.org/10.1107/S0907444996012255	journal	May 1997
Overview of the CCP 4 suite and current developments Winn, Martyn D.; Ballard, Charles C.; Cowtan, Kevin D. Acta Crystallographica Section D Biological Crystallography, Vol. 67, Issue 4 https://doi.org/10.1107/S0907444910045749	journal	March 2011
Insights from the sea: Structural biology of marine polyketide synthases Akey, David L.; Gehret, Jennifer J.; Khare, Dheeraj Natural Product Reports, Vol. 29, Issue 10 https://doi.org/10.1039/c2np20016c	journal	January 2012
Drug Discovery from Marine Microbes Gerwick, William H.; Fenner, Amanda M. Microbial Ecology, Vol. 65, Issue 4 https://doi.org/10.1007/s00248-012-0169-9	journal	December 2012
The Biosynthetic Logic of Polyketide Diversity Hertweck, Christian Angewandte Chemie International Edition, Vol. 48, Issue 26 https://doi.org/10.1002/anie.200806121	journal	June 2009
New tricks from ancient algae: natural products biosynthesis in marine cyanobacteria Jones, Adam C.; Gu, Liangcai; Sorrels, Carla M. Current Opinion in Chemical Biology, Vol. 13, Issue 2 https://doi.org/10.1016/j.cbpa.2009.02.019	journal	April 2009
Medium-chain dehydrogenases/reductases (MDR): Family characterizations including genome comparisons and active site modelling Nordling, Erik; Jörnvall, Hans; Persson, Bengt European Journal of Biochemistry, Vol. 269, Issue 17 https://doi.org/10.1046/j.1432-1033.2002.03114.x	journal	August 2002
The use of ene adducts to study and engineer enoyl-thioester reductases Rosenthal, Raoul G.; Vögeli, Bastian; Quade, Nick Nature Chemical Biology, Vol. 11, Issue 6 https://doi.org/10.1038/nchembio.1794	journal	April 2015
BALBES : a molecular-replacement pipeline Long, Fei; Vagin, Alexei A.; Young, Paul Acta Crystallographica Section D Biological Crystallography, Vol. 64, Issue 1 https://doi.org/10.1107/S0907444907050172	journal	December 2007
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
Lessons from the Past and Charting the Future of Marine Natural Products Drug Discovery and Chemical Biology Gerwick, William H.; Moore, Bradley S. Chemistry & Biology, Vol. 19, Issue 1 https://doi.org/10.1016/j.chembiol.2011.12.014	journal	January 2012
Structure and Biosynthesis of the Jamaicamides, New Mixed Polyketide-Peptide Neurotoxins from the Marine Cyanobacterium Lyngbya majuscula Edwards, Daniel J.; Marquez, Brian L.; Nogle, Lisa M. Chemistry & Biology, Vol. 11, Issue 6 https://doi.org/10.1016/j.chembiol.2004.03.030	journal	June 2004
Crystal structure and biochemical studies of the trans-acting polyketide enoyl reductase LovC from lovastatin biosynthesis Ames, B. D.; Nguyen, C.; Bruegger, J. Proceedings of the National Academy of Sciences, Vol. 109, Issue 28 https://doi.org/10.1073/pnas.1113029109	journal	June 2012
HOLLOW: Generating Accurate Representations of Channel and Interior Surfaces in Molecular Structures Ho, Bosco K.; Gruswitz, Franz BMC Structural Biology, Vol. 8, Issue 1 https://doi.org/10.1186/1472-6807-8-49	journal	January 2008
Metamorphic enzyme assembly in polyketide diversification Gu, Liangcai; Wang, Bo; Kulkarni, Amol Nature, Vol. 459, Issue 7247 https://doi.org/10.1038/nature07870	journal	June 2009
Synthesis of C₅-dicarboxylic acids from C₂-units involving crotonyl-CoA carboxylase/reductase: The ethylmalonyl-CoA pathway Erb, T. J.; Berg, I. A.; Brecht, V. Proceedings of the National Academy of Sciences, Vol. 104, Issue 25, p. 10631-10636 https://doi.org/10.1073/pnas.0702791104	journal	June 2007
PHENIX: a comprehensive Python-based system for macromolecular structure solution Adams, Paul D.; Afonine, Pavel V.; Bunkóczi, Gábor Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2, p. 213-221 https://doi.org/10.1107/S0907444909052925	journal	January 2010
Crystal Structure ofEscherichia coliQOR Quinone Oxidoreductase Complexed with NADPH Thorn, Jennifer M.; Barton, John D.; Dixon, Nicholas E. Journal of Molecular Biology, Vol. 249, Issue 4 https://doi.org/10.1006/jmbi.1995.0337	journal	June 1995
Prediction and Manipulation of the Stereochemistry of Enoylreduction in Modular Polyketide Synthases Kwan, David H.; Sun, Yuhui; Schulz, Frank Chemistry & Biology, Vol. 15, Issue 11 https://doi.org/10.1016/j.chembiol.2008.09.012	journal	November 2008
Moorea producens gen. nov., sp. nov. and Moorea bouillonii comb. nov., tropical marine cyanobacteria rich in bioactive secondary metabolites Engene, N.; Rottacker, E. C.; Kastovsky, J. INTERNATIONAL JOURNAL OF SYSTEMATIC AND EVOLUTIONARY MICROBIOLOGY, Vol. 62, Issue Pt 5 https://doi.org/10.1099/ijs.0.033761-0	journal	July 2011
Subdivision of the MDR superfamily of medium-chain dehydrogenases/reductases through iterative hidden Markov model refinement Hedlund, Joel; Jörnvall, Hans; Persson, Bengt BMC Bioinformatics, Vol. 11, Issue 1 https://doi.org/10.1186/1471-2105-11-534	journal	October 2010
The Crystal Structure of a Mammalian Fatty Acid Synthase Maier, T.; Leibundgut, M.; Ban, N. Science, Vol. 321, Issue 5894 https://doi.org/10.1126/science.1161269	journal	September 2008
Medium- and short-chain dehydrogenase/reductase gene and protein families: The MDR superfamily Persson, B.; Hedlund, J.; Jörnvall, H. Cellular and Molecular Life Sciences, Vol. 65, Issue 24 https://doi.org/10.1007/s00018-008-8587-z	journal	November 2008
Direct evidence for a covalent ene adduct intermediate in NAD(P)H-dependent enzymes Rosenthal, Raoul G.; Ebert, Marc-Olivier; Kiefer, Patrick Nature Chemical Biology, Vol. 10, Issue 1 https://doi.org/10.1038/nchembio.1385	journal	November 2013
The barbamide biosynthetic gene cluster: a novel marine cyanobacterial system of mixed polyketide synthase (PKS)-non-ribosomal peptide synthetase (NRPS) origin involving an unusual trichloroleucyl starter unit Chang, Zunxue; Flatt, Patricia; Gerwick, William H. Gene, Vol. 296, Issue 1-2 https://doi.org/10.1016/S0378-1119(02)00860-0	journal	August 2002
MolProbity: all-atom contacts and structure validation for proteins and nucleic acids Davis, I. W.; Leaver-Fay, A.; Chen, V. B. Nucleic Acids Research, Vol. 35, Issue Web Server https://doi.org/10.1093/nar/gkm216	journal	May 2007
Unusual carbon fixation gives rise to diverse polyketide extender units Quade, Nick; Huo, Liujie; Rachid, Shwan Nature Chemical Biology, Vol. 8, Issue 1 https://doi.org/10.1038/nchembio.734	journal	December 2011
Searching protein structure databases with DaliLite v.3 Holm, L.; Kaariainen, S.; Rosenstrom, P. Bioinformatics, Vol. 24, Issue 23 https://doi.org/10.1093/bioinformatics/btn507	journal	September 2008
A New Vector for High-Throughput, Ligation-Independent Cloning Encoding a Tobacco Etch Virus Protease Cleavage Site Stols, Lucy; Gu, Minyi; Dieckman, Lynda Protein Expression and Purification, Vol. 25, Issue 1 https://doi.org/10.1006/prep.2001.1603	journal	June 2002
Biosynthetic Pathway and Gene Cluster Analysis of Curacin A, an Antitubulin Natural Product from the Tropical Marine Cyanobacterium Lyngbya majuscula Chang, Zunxue; Sitachitta, Namthip; Rossi, James V. Journal of Natural Products, Vol. 67, Issue 8, p. 1356-1367 https://doi.org/10.1021/np0499261	journal	August 2004
New antibiotics from bacterial natural products Clardy, Jon; Fischbach, Michael A.; Walsh, Christopher T. Nature Biotechnology, Vol. 24, Issue 12 https://doi.org/10.1038/nbt1266	journal	December 2006
Metabolic Coupling of Dehydration and Decarboxylation in the Curacin A Pathway: Functional Identification of a Mechanistically Diverse Enzyme Pair Gu, Liangcai; Jia, Junyong; Liu, Haichuan Journal of the American Chemical Society, Vol. 128, Issue 28 https://doi.org/10.1021/ja0626382	journal	July 2006
Crystal Structure of Anti-Configuration of Indomethacin and Leukotriene B4 12-Hydroxydehydrogenase/15-Oxo-Prostaglandin 13-Reductase Complex Reveals the Structural Basis of Broad Spectrum Indomethacin Efficacy Hori, Tetsuya; Ishijima, Jun; Yokomizo, Takehiko The Journal of Biochemistry, Vol. 140, Issue 3 https://doi.org/10.1093/jb/mvj176	journal	September 2006
XDS Kabsch, Wolfgang Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2 https://doi.org/10.1107/S0907444909047337	journal	January 2010
LigPlot+: Multiple Ligand–Protein Interaction Diagrams for Drug Discovery Laskowski, Roman A.; Swindells, Mark B. Journal of Chemical Information and Modeling, Vol. 51, Issue 10 https://doi.org/10.1021/ci200227u	journal	October 2011
Mutagenesis of a Modular Polyketide Synthase Enoylreductase Domain Reveals Insights into Catalysis and Stereospecificity Kwan, David H.; Leadlay, Peter F. ACS Chemical Biology, Vol. 5, Issue 9 https://doi.org/10.1021/cb100175a	journal	July 2010
Three-dimensional Structure and Enzymatic Function of Proapoptotic Human p53-inducible Quinone Oxidoreductase PIG3 Porté, Sergio; Valencia, Eva; Yakovtseva, Evgenia A. Journal of Biological Chemistry, Vol. 284, Issue 25 https://doi.org/10.1074/jbc.M109.001800	journal	June 2009
Structure of Three Class I Human Alcohol Dehydrogenases Complexed with Isoenzyme Specific Formamide Inhibitors ^† ^, ^‡ Gibbons, Brian J.; Hurley, Thomas D. Biochemistry, Vol. 43, Issue 39 https://doi.org/10.1021/bi0489107	journal	October 2004
[20] Processing of X-ray diffraction data collected in oscillation mode Otwinowski, Zbyszek; Minor, Wladek Macromolecular Crystallography Part A, 307-326 https://doi.org/10.1016/S0076-6879(97)76066-X	book	January 1997
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
Mocr: A novel fusion tag for enhancing solubility that is compatible with structural biology applications DelProposto, James; Majmudar, Chinmay Y.; Smith, Janet L. Protein Expression and Purification, Vol. 63, Issue 1 https://doi.org/10.1016/j.pep.2008.08.011	journal	January 2009
Assembly-Line Enzymology for Polyketide and Nonribosomal Peptide Antibiotics: Logic, Machinery, and Mechanisms Fischbach, Michael A.; Walsh, Christopher T. Chemical Reviews, Vol. 106, Issue 8 https://doi.org/10.1021/cr0503097	journal	August 2006
Conformational switch triggered by -ketoglutarate in a halogenase of curacin A biosynthesis Khare, D.; Wang, B.; Gu, L. Proceedings of the National Academy of Sciences, Vol. 107, Issue 32 https://doi.org/10.1073/pnas.1006738107	journal	July 2010
Natural Products As Sources of New Drugs over the 30 Years from 1981 to 2010 Newman, David J.; Cragg, Gordon M. Journal of Natural Products, Vol. 75, Issue 3 https://doi.org/10.1021/np200906s	journal	January 2012
Crystal Structure of the ECH2 Catalytic Domain of CurF from Lyngbya majuscula Geders, Todd W.; Gu, Liangcai; Mowers, Jonathan C. Journal of Biological Chemistry, Vol. 282, Issue 49 https://doi.org/10.1074/jbc.M703921200	journal	December 2007

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