Reprogramming the Cyclization Cascade of epi -Isozizaene Synthase to Generate Alternative Terpene Products

Eaton, Samuel A.; Christianson, David W.

doi:10.1021/acs.biochem.3c00247

Reprogramming the Cyclization Cascade of epi -Isozizaene Synthase to Generate Alternative Terpene Products

Journal Article · 14 July 2023 · Biochemistry

DOI:https://doi.org/10.1021/acs.biochem.3c00247· OSTI ID:2423584

^[1]; ^[1]

Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States

Not provided.

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC02-06CH11357

OSTI ID:: 2423584

Journal Information:: Biochemistry, Journal Name: Biochemistry Journal Issue: 15 Vol. 62; ISSN 0006-2960

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (50)

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
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
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
Chain elongation in the isoprenoid biosynthetic pathway Kellogg, Brenda A.; Poulter, C. Dale Current Opinion in Chemical Biology, Vol. 1, Issue 4 https://doi.org/10.1016/S1367-5931(97)80054-3	journal	December 1997
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
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
Techno-economic analysis and life-cycle greenhouse gas mitigation cost of five routes to bio-jet fuel blendstocks Baral, Nawa Raj; Kavvada, Olga; Mendez-Perez, Daniel Energy & Environmental Science, Vol. 12, Issue 3 https://doi.org/10.1039/C8EE03266A	journal	January 2019
The isoprene rule and the biogenesis of terpenic compounds Ruzicka, L. Experientia, Vol. 9, Issue 10 https://doi.org/10.1007/BF02167631	journal	October 1953
High-Density Renewable Diesel and Jet Fuels Prepared from Multicyclic Sesquiterpanes and a 1-Hexene-Derived Synthetic Paraffinic Kerosene Harvey, Benjamin G.; Merriman, Walter W.; Koontz, Thomas A. Energy & Fuels, Vol. 29, Issue 4 https://doi.org/10.1021/ef5027746	journal	March 2015
The menthol receptor TRPM8 is the principal detector of environmental cold Bautista, Diana M.; Siemens, Jan; Glazer, Joshua M. Nature, Vol. 448, Issue 7150 https://doi.org/10.1038/nature05910	journal	May 2007
MolProbity : all-atom structure validation for macromolecular crystallography Chen, Vincent B.; Arendall, W. Bryan; Headd, Jeffrey J. Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 1 https://doi.org/10.1107/S0907444909042073	journal	December 2009
Identification and microbial production of a terpene-based advanced biofuel Peralta-Yahya, Pamela P.; Ouellet, Mario; Chan, Rossana Nature Communications, Vol. 2, Issue 1 https://doi.org/10.1038/ncomms1494	journal	September 2011
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
CHEMISTRY: Roots of Biosynthetic Diversity Christianson, D. W. Science, Vol. 316, Issue 5821 https://doi.org/10.1126/science.1141630	journal	April 2007
Crystal Structure of Pentalenene Synthase: Mechanistic Insights on Terpenoid Cyclization Reactions in Biology Lesburg, C. A. Science, Vol. 277, Issue 5333 https://doi.org/10.1126/science.277.5333.1820	journal	September 1997
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
Trinuclear metal clusters in catalysis by terpenoid synthases Aaron, Julie A.; Christianson, David W. Pure and Applied Chemistry, Vol. 82, Issue 8 https://doi.org/10.1351/PAC-CON-09-09-37	journal	May 2010
Isoprenoid Drugs, Biofuels, and Chemicals—Artemisinin, Farnesene, and Beyond George, Kevin W.; Alonso-Gutierrez, Jorge; Keasling, Jay D. Biotechnology of Isoprenoids https://doi.org/10.1007/10_2014_288	book	January 2015
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
XDS Kabsch, Wolfgang Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2 https://doi.org/10.1107/S0907444909047337	journal	January 2010
Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants Degenhardt, Jörg; Köllner, Tobias G.; Gershenzon, Jonathan Phytochemistry, Vol. 70, Issue 15-16 https://doi.org/10.1016/j.phytochem.2009.07.030	journal	October 2009
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
Menthol - Pharmacology of an Important Naturally Medicinal “Cool” A. Farco, Joseph; Grundmann, Oliver Mini Reviews in Medicinal Chemistry, Vol. 13, Issue 1 https://doi.org/10.2174/138955713804484686	journal	January 2013
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
Natural product biosynthesis: What's next? An introduction to the JBC Reviews Thematic Series Nair, Satish K.; Jez, Joseph M. Journal of Biological Chemistry, Vol. 295, Issue 2 https://doi.org/10.1074/jbc.REV119.011586	journal	January 2020
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
The prenyl transfer reaction. Enzymic and mechanistic studies of the 1'-4 coupling reaction in the terpene biosynthetic pathway Poulter, C. Dale; Rilling, Hans C. Accounts of Chemical Research, Vol. 11, Issue 8 https://doi.org/10.1021/ar50128a004	journal	August 1978
BIOCHEMISTRY: Creating Isoprenoid Diversity Sacchettini, J. C. Science, Vol. 277, Issue 5333 https://doi.org/10.1126/science.277.5333.1788	journal	September 1997
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
An Aromatic Cluster in the Active Site of epi-Isozizaene Synthase Is an Electrostatic Toggle for Divergent Terpene Cyclization Pathways Ronnebaum, Trey A.; Gardner, Sarah M.; Christianson, David W. Biochemistry, Vol. 59, Issue 50 https://doi.org/10.1021/acs.biochem.0c00876	journal	December 2020
Enzyme Mechanisms for Triterpene Cyclization: New Pieces of the Puzzle Wendt, K. Ulrich Angewandte Chemie International Edition, Vol. 44, Issue 26 https://doi.org/10.1002/anie.200500804	journal	June 2005
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
Mechanism of action of taxol Band Horwitz, Susan Trends in Pharmacological Sciences, Vol. 13 https://doi.org/10.1016/0165-6147(92)90048-B	journal	January 1992
Terpene synthases and the regulation, diversity and biological roles of terpene metabolism Tholl, Dorothea Current Opinion in Plant Biology, Vol. 9, Issue 3 https://doi.org/10.1016/j.pbi.2006.03.014	journal	June 2006
Structure and Function of a Squalene Cyclase Wendt, K. U. Science, Vol. 277, Issue 5333 https://doi.org/10.1126/science.277.5333.1811	journal	September 1997
Menthol: A refreshing look at this ancient compound Patel, Tejesh; Ishiuji, Yozo; Yosipovitch, Gil Journal of the American Academy of Dermatology, Vol. 57, Issue 5 https://doi.org/10.1016/j.jaad.2007.04.008	journal	November 2007
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
A TRP Channel that Senses Cold Stimuli and Menthol Peier, Andrea M.; Moqrich, Aziz; Hergarden, Anne C. Cell, Vol. 108, Issue 5 https://doi.org/10.1016/S0092-8674(02)00652-9	journal	March 2002
Engineering Terpene Biosynthesis in Streptomyces for Production of the Advanced Biofuel Precursor Bisabolene Phelan, Ryan M.; Sekurova, Olga N.; Keasling, Jay D. ACS Synthetic Biology, Vol. 4, Issue 4 https://doi.org/10.1021/sb5002517	journal	July 2014
The birth of artemisinin Ma, Nan; Zhang, Ziyue; Liao, Fulong Pharmacology & Therapeutics, Vol. 216 https://doi.org/10.1016/j.pharmthera.2020.107658	journal	December 2020
Harnessing Nature's wisdom Hunter, Philip EMBO reports, Vol. 9, Issue 9 https://doi.org/10.1038/embor.2008.160	journal	September 2008
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
Structural Basis for Cyclic Terpene Biosynthesis by Tobacco 5-Epi-Aristolochene Synthase Starks, C. M. Science, Vol. 277, Issue 5333 https://doi.org/10.1126/science.277.5333.1815	journal	September 1997
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
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
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
Plant antitumor agents. VI. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia Wani, Mansukhlal C.; Taylor, Harold Lawrence; Wall, Monroe E. Journal of the American Chemical Society, Vol. 93, Issue 9 https://doi.org/10.1021/ja00738a045	journal	May 1971
Taxol stabilizes microtubules in mouse fibroblast cells. Schiff, P. B.; Horwitz, S. B. Proceedings of the National Academy of Sciences, Vol. 77, Issue 3 https://doi.org/10.1073/pnas.77.3.1561	journal	March 1980
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
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

Similar Records

Reprogramming the Chemodiversity of Terpenoid Cyclization by Remolding the Active Site Contour of epi-Isozizaene Synthase

Journal Article · 2014 · Biochemistry-US · OSTI ID:1130092

Reprogramming the Chemodiversity of Terpenoid Cyclization by Remolding the Active Site Contour of epi-Isozizaene Synthase

Journal Article · 2014 · Biochemistry · OSTI ID:1162838

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

Journal Article · 2021 · Biochemistry · OSTI ID:1760529

Related Subjects

Biochemistry & Molecular Biology

Reprogramming the Cyclization Cascade of epi -Isozizaene Synthase to Generate Alternative Terpene Products

Citation Formats

References (50)

Similar Records

Related Subjects