An Aromatic Cluster in the Active Site of epi-Isozizaene Synthase Is an Electrostatic Toggle for Divergent Terpene Cyclization Pathways

Ronnebaum, T; Gardner, S.; Christianson, D.

doi:10.1021/acs.biochem.0c00876

An Aromatic Cluster in the Active Site of epi-Isozizaene Synthase Is an Electrostatic Toggle for Divergent Terpene Cyclization Pathways

Journal Article · 01 January 2022 · Biochemistry

DOI:https://doi.org/10.1021/acs.biochem.0c00876· OSTI ID:1760529

Ronnebaum, T; Gardner, S.; Christianson, D.

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

Sponsoring Organization:: ~OTHER

DOE Contract Number:: SC0012704

OSTI ID:: 1760529

Report Number(s):: BNL-220877-2021-JACI

Journal Information:: Biochemistry, Vol. 59, Issue 50

Country of Publication:: United States

Language:: English

References (38)

Structural Biology and Chemistry of the Terpenoid Cyclases Christianson, David W. Chemical Reviews, Vol. 106, Issue 8 https://doi.org/10.1021/cr050286w	journal	August 2006
Structural and Chemical Biology of Terpenoid Cyclases Christianson, David W. Chemical Reviews, Vol. 117, Issue 17 https://doi.org/10.1021/acs.chemrev.7b00287	journal	August 2017
Terpenoid synthase structures: a so far incomplete view of complex catalysis Gao, Yang; Honzatko, Richard B.; Peters, Reuben J. Natural Product Reports, Vol. 29, Issue 10 https://doi.org/10.1039/c2np20059g	journal	January 2012
Defining the Product Chemical Space of Monoterpenoid Synthases Tian, Boxue; Poulter, C. Dale; Jacobson, Matthew P. PLOS Computational Biology, Vol. 12, Issue 8 https://doi.org/10.1371/journal.pcbi.1005053	journal	August 2016
The function of terpene natural products in the natural world Gershenzon, Jonathan; Dudareva, Natalia Nature Chemical Biology, Vol. 3, Issue 7 https://doi.org/10.1038/nchembio.2007.5	journal	June 2007
Biosynthesis of Plant Volatiles: Nature's Diversity and Ingenuity Pichersky, E. Science, Vol. 311, Issue 5762 https://doi.org/10.1126/science.1118510	journal	February 2006
Traversing the fungal terpenome Quin, Maureen B.; Flynn, Christopher M.; Schmidt-Dannert, Claudia Nat. Prod. Rep., Vol. 31, Issue 10 https://doi.org/10.1039/C4NP00075G	journal	January 2014
‘Hidden’ Terpenoids in Plants: Their Biosynthesis, Localization and Ecological Roles Yazaki, Kazufumi; Arimura, Gen-ichiro; Ohnishi, Toshiyuki Plant and Cell Physiology, Vol. 58, Issue 10 https://doi.org/10.1093/pcp/pcx123	journal	August 2017
Terpenes and isoprenoids: a wealth of compounds for global use Tetali, Sarada D. Planta, Vol. 249, Issue 1 https://doi.org/10.1007/s00425-018-3056-x	journal	November 2018
Promotion of microtubule assembly in vitro by taxol Schiff, Peter B.; Fant, Jane; Horwitz, Susan B. Nature, Vol. 277, Issue 5698 https://doi.org/10.1038/277665a0	journal	February 1979
Artemisinin-A Gift from Traditional Chinese Medicine to the World (Nobel Lecture) Tu, Youyou Angewandte Chemie International Edition, Vol. 55, Issue 35 https://doi.org/10.1002/anie.201601967	journal	August 2016
Understanding Synergistic Toxicity of Terpenes as Insecticides: Contribution of Metabolic Detoxification in Musca domestica Scalerandi, Esteban; Flores, Guillermo A.; Palacio, Marcela Frontiers in Plant Science, Vol. 9 https://doi.org/10.3389/fpls.2018.01579	journal	October 2018
Use of Novel Compounds for Pest Control: Insecticidal and Acaricidal Activity of Essential Oil Components from Heartwood of Alaska Yellow Cedar Panella, Nicholas A.; Dolan, Marc C.; Karchesy, Joseph J. Journal of Medical Entomology, Vol. 42, Issue 3 https://doi.org/10.1093/jmedent/42.3.352	journal	May 2005
Alteration of product formation by directed mutagenesis and truncation of the multiple-product sesquiterpene synthases δ-selinene synthase and γ-humulene synthase Little, Dawn B.; Croteau, Rodney B. Archives of Biochemistry and Biophysics, Vol. 402, Issue 1 https://doi.org/10.1016/S0003-9861(02)00068-1	journal	June 2002
Tomato-produced 7-epizingiberene and R-curcumene act as repellents to whiteflies Bleeker, Petra M.; Diergaarde, Paul J.; Ament, Kai Phytochemistry, Vol. 72, Issue 1 https://doi.org/10.1016/j.phytochem.2010.10.014	journal	January 2011
Essential Oils and Anxiolytic Aromatherapy Setzer, William N. Natural Product Communications, Vol. 4, Issue 9 https://doi.org/10.1177/1934578X0900400928	journal	September 2009
Plant-Derived Terpenes: A Feedstock for Specialty Biofuels Mewalal, Ritesh; Rai, Durgesh K.; Kainer, David Trends in Biotechnology, Vol. 35, Issue 3 https://doi.org/10.1016/j.tibtech.2016.08.003	journal	March 2017
Leveraging microbial biosynthetic pathways for the generation of ‘drop-in’ biofuels Zargar, Amin; Bailey, Constance B.; Haushalter, Robert W. Current Opinion in Biotechnology, Vol. 45 https://doi.org/10.1016/j.copbio.2017.03.004	journal	June 2017
Chemical transformations of characteristic hop secondary metabolites in relation to beer properties and the brewing process: A review Steenackers, Bart; De Cooman, Luc; De Vos, Dirk Food Chemistry, Vol. 172 https://doi.org/10.1016/j.foodchem.2014.09.139	journal	April 2015
Cannabis sativa: The Plant of the Thousand and One Molecules Andre, Christelle M.; Hausman, Jean-Francois; Guerriero, Gea Frontiers in Plant Science, Vol. 7 https://doi.org/10.3389/fpls.2016.00019	journal	February 2016
Terpene synthases from Cannabis sativa Booth, Judith K.; Page, Jonathan E.; Bohlmann, Jörg PLOS ONE, Vol. 12, Issue 3 https://doi.org/10.1371/journal.pone.0173911	journal	March 2017
Structure of Epi-Isozizaene Synthase from Streptomyces coelicolor A3(2), a Platform for New Terpenoid Cyclization Templates ^, Aaron, Julie A.; Lin, Xin; Cane, David E. Biochemistry, Vol. 49, Issue 8 https://doi.org/10.1021/bi902088z	journal	March 2010
Biosynthesis of the Sesquiterpene Antibiotic Albaflavenone in Streptomyces coelicolor . Mechanism and Stereochemistry of the Enzymatic Formation of Epi-isozizaene Lin, Xin; Cane, David E. Journal of the American Chemical Society, Vol. 131, Issue 18 https://doi.org/10.1021/ja901313v	journal	May 2009
Genome Mining in Streptomyces c oelicolor : Molecular Cloning and Characterization of a New Sesquiterpene Synthase Lin, Xin; Hopson, Russell; Cane, David E. Journal of the American Chemical Society, Vol. 128, Issue 18 https://doi.org/10.1021/ja061292s	journal	May 2006
Reprogramming the Chemodiversity of Terpenoid Cyclization by Remolding the Active Site Contour of epi -Isozizaene Synthase Li, Ruiqiong; Chou, Wayne K. W.; Himmelberger, Julie A. Biochemistry, Vol. 53, Issue 7 https://doi.org/10.1021/bi401643u	journal	February 2014
Substitution of Aromatic Residues with Polar Residues in the Active Site Pocket of epi -Isozizaene Synthase Leads to the Generation of New Cyclic Sesquiterpenes Blank, Patrick N.; Barrow, Golda H.; Chou, Wayne K. W. Biochemistry, Vol. 56, Issue 43 https://doi.org/10.1021/acs.biochem.7b00895	journal	October 2017
iMOSFLM : a new graphical interface for diffraction-image processing with MOSFLM Battye, T. Geoff G.; Kontogiannis, Luke; Johnson, Owen Acta Crystallographica Section D Biological Crystallography, Vol. 67, Issue 4 https://doi.org/10.1107/S0907444910048675	journal	March 2011
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
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
Features and development of Coot Emsley, P.; Lohkamp, B.; Scott, W. G. Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 4 https://doi.org/10.1107/S0907444910007493	journal	March 2010
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
NRGsuite: a PyMOL plugin to perform docking simulations in real time using FlexAID Gaudreault, Francis; Morency, Louis-Philippe; Najmanovich, Rafael J. Bioinformatics https://doi.org/10.1093/bioinformatics/btv458	journal	August 2015
electronic Ligand Builder and Optimization Workbench ( eLBOW ): a tool for ligand coordinate and restraint generation Moriarty, Nigel W.; Grosse-Kunstleve, Ralf W.; Adams, Paul D. Acta Crystallographica Section D Biological Crystallography, Vol. 65, Issue 10 https://doi.org/10.1107/S0907444909029436	journal	September 2009
Volume changes on protein folding Harpaz, Yehouda; Gerstein, Mark; Chothia, Cyrus Structure, Vol. 2, Issue 7 https://doi.org/10.1016/S0969-2126(00)00065-4	journal	July 1994
The interaction between methionine and two aromatic amino acids is an abundant and multifunctional motif in proteins Weber, David S.; Warren, Jeffrey J. Archives of Biochemistry and Biophysics, Vol. 672 https://doi.org/10.1016/j.abb.2019.07.018	journal	September 2019
Models of S/π interactions in protein structures: Comparison of the H ₂ S-benzene complex with PDB data Ringer, Ashley L.; Senenko, Anastasia; Sherrill, C. David Protein Science, Vol. 16, Issue 10 https://doi.org/10.1110/ps.073002307	journal	October 2007
The Methionine-aromatic Motif Plays a Unique Role in Stabilizing Protein Structure Valley, Christopher C.; Cembran, Alessandro; Perlmutter, Jason D. Journal of Biological Chemistry, Vol. 287, Issue 42 https://doi.org/10.1074/jbc.M112.374504	journal	August 2012
Crystal structure of F95Q epi-isozizaene synthase, an engineered sesquiterpene cyclase that generates biofuel precursors β- and γ-curcumene Blank, Patrick N.; Barrow, Golda H.; Christianson, David W. Journal of Structural Biology, Vol. 207, Issue 2 https://doi.org/10.1016/j.jsb.2019.05.011	journal	August 2019

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