Search Menu
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information
Search Scholarly Publications

Title: Terpene Synthases as Metabolic Gatekeepers in the Evolution of Plant Terpenoid Chemical Diversity

Abstract

Terpenoids comprise tens of thousands of small molecule natural products that are widely distributed across all domains of life. Plants produce by far the largest array of terpenoids with various roles in development and chemical ecology. Driven by selective pressure to adapt to their specific ecological niche, individual species form only a fraction of the myriad plant terpenoids, typically representing unique metabolite blends. Terpene synthase (TPS) enzymes are the gatekeepers in generating terpenoid diversity by catalyzing complex carbocation-driven cyclization, rearrangement, and elimination reactions that enable the transformation of a few acyclic prenyl diphosphate substrates into a vast chemical library of hydrocarbon and, for a few enzymes, oxygenated terpene scaffolds. The seven currently defined clades (a-h) forming the plant TPS family evolved from ancestral triterpene synthase- and prenyl transferase-type enzymes through repeated events of gene duplication and subsequent loss, gain, or fusion of protein domains and further functional diversification. Lineage-specific expansion of these TPS clades led to variable family sizes that may range from a single TPS gene to families of more than 100 members that may further function as part of modular metabolic networks to maximize the number of possible products. Accompanying gene family expansion, the TPS family shows amore » profound functional plasticity, where minor active site alterations can dramatically impact product outcome, thus enabling the emergence of new functions with minimal investment in evolving new enzymes. This article reviews current knowledge on the functional diversity and molecular evolution of the plant TPS family that underlies the chemical diversity of bioactive terpenoids across the plant kingdom.« less

Authors:
;
Publication Date:
Research Org.:
Univ. of California, Davis, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER). Biological Systems Science Division
OSTI Identifier:
1567897
Alternate Identifier(s):
OSTI ID: 1633652
Grant/Contract Number:  
SC0019178
Resource Type:
Published Article
Journal Name:
Frontiers in Plant Science
Additional Journal Information:
Journal Name: Frontiers in Plant Science Journal Volume: 10; Journal ID: ISSN 1664-462X
Publisher:
Frontiers Research Foundation
Country of Publication:
Switzerland
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; terpenoids; terpene synthases; plant specialized metabolism; plant chemical diversity; terpenoid biosynthesis; natural products

Citation Formats

Karunanithi, Prema S., and Zerbe, Philipp. Terpene Synthases as Metabolic Gatekeepers in the Evolution of Plant Terpenoid Chemical Diversity. Switzerland: N. p., 2019. Web. doi:10.3389/fpls.2019.01166.
Copy to clipboard
Karunanithi, Prema S., & Zerbe, Philipp. Terpene Synthases as Metabolic Gatekeepers in the Evolution of Plant Terpenoid Chemical Diversity. Switzerland. https://doi.org/10.3389/fpls.2019.01166
Copy to clipboard
Karunanithi, Prema S., and Zerbe, Philipp. Tue . "Terpene Synthases as Metabolic Gatekeepers in the Evolution of Plant Terpenoid Chemical Diversity". Switzerland. https://doi.org/10.3389/fpls.2019.01166.
Copy to clipboard
@article{osti_1567897,
title = {Terpene Synthases as Metabolic Gatekeepers in the Evolution of Plant Terpenoid Chemical Diversity},
author = {Karunanithi, Prema S. and Zerbe, Philipp},
abstractNote = {Terpenoids comprise tens of thousands of small molecule natural products that are widely distributed across all domains of life. Plants produce by far the largest array of terpenoids with various roles in development and chemical ecology. Driven by selective pressure to adapt to their specific ecological niche, individual species form only a fraction of the myriad plant terpenoids, typically representing unique metabolite blends. Terpene synthase (TPS) enzymes are the gatekeepers in generating terpenoid diversity by catalyzing complex carbocation-driven cyclization, rearrangement, and elimination reactions that enable the transformation of a few acyclic prenyl diphosphate substrates into a vast chemical library of hydrocarbon and, for a few enzymes, oxygenated terpene scaffolds. The seven currently defined clades (a-h) forming the plant TPS family evolved from ancestral triterpene synthase- and prenyl transferase-type enzymes through repeated events of gene duplication and subsequent loss, gain, or fusion of protein domains and further functional diversification. Lineage-specific expansion of these TPS clades led to variable family sizes that may range from a single TPS gene to families of more than 100 members that may further function as part of modular metabolic networks to maximize the number of possible products. Accompanying gene family expansion, the TPS family shows a profound functional plasticity, where minor active site alterations can dramatically impact product outcome, thus enabling the emergence of new functions with minimal investment in evolving new enzymes. This article reviews current knowledge on the functional diversity and molecular evolution of the plant TPS family that underlies the chemical diversity of bioactive terpenoids across the plant kingdom.},
doi = {10.3389/fpls.2019.01166},
journal = {Frontiers in Plant Science},
number = ,
volume = 10,
place = {Switzerland},
year = {2019},
month = {10}
}
Copy to clipboard
Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.3389/fpls.2019.01166
Copyright Statement
Other availability
Search WorldCat Search WorldCat to find libraries that may hold this journal
Citation Metrics:
Cited by: 13 works
Citation information provided by
Web of Science
Save / Share:
Export Metadata
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.

Works referenced in this record:

Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis
journal, December 2010

  • Köksal, Mustafa; Jin, Yinghua; Coates, Robert M.
  • Nature, Vol. 469, Issue 7328
  • DOI: 10.1038/nature09628

Terpene synthase genes in eukaryotes beyond plants and fungi: Occurrence in social amoebae
journal, October 2016

  • Chen, Xinlu; Köllner, Tobias G.; Jia, Qidong
  • Proceedings of the National Academy of Sciences, Vol. 113, Issue 43
  • DOI: 10.1073/pnas.1610379113

Functional divergence of diterpene syntheses in the medicinal plant Salvia miltiorrhiza Bunge
journal, June 2015

Chrysanthemyl diphosphate synthase: Isolation of the gene and characterization of the recombinant non-head-to-tail monoterpene synthase from Chrysanthemum cinerariaefolium
journal, April 2001

  • Rivera, S. B.; Swedlund, B. D.; King, G. J.
  • Proceedings of the National Academy of Sciences, Vol. 98, Issue 8
  • DOI: 10.1073/pnas.071543598

Terpenoid metabolism.
journal, July 1995

Breaking new ground in the regulation of the early steps of plant isoprenoid biosynthesis
journal, June 2015

Plant metabolism, the diverse chemistry set of the future
journal, September 2016

The Eucalyptus terpene synthase gene family
journal, June 2015

Long-distance signalling in plant defence
journal, June 2008

Demonstration That Menthofuran Synthase of Mint (Mentha) Is a Cytochrome P450 Monooxygenase: Cloning, Functional Expression, and Characterization of the Responsible Gene
journal, June 2001

  • Bertea, Cinzia M.; Schalk, Michel; Karp, Frank
  • Archives of Biochemistry and Biophysics, Vol. 390, Issue 2
  • DOI: 10.1006/abbi.2001.2378

Orthologs of the archaeal isopentenyl phosphate kinase regulate terpenoid production in plants
journal, July 2015

  • Henry, Laura K.; Gutensohn, Michael; Thomas, Suzanne T.
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 32
  • DOI: 10.1073/pnas.1504798112

Structure of the ent -Copalyl Diphosphate Synthase PtmT2 from Streptomyces platensis CB00739, a Bacterial Type II Diterpene Synthase
journal, August 2016

  • Rudolf, Jeffrey D.; Dong, Liao-Bin; Cao, Hongnan
  • Journal of the American Chemical Society, Vol. 138, Issue 34
  • DOI: 10.1021/jacs.6b04317

Lettuce Costunolide Synthase ( CYP71BL2 ) and Its Homolog ( CYP71BL1 ) from Sunflower Catalyze Distinct Regio- and Stereoselective Hydroxylations in Sesquiterpene Lactone Metabolism
journal, April 2011

  • Ikezawa, Nobuhiro; Göpfert, Jens Christian; Nguyen, Don Trinh
  • Journal of Biological Chemistry, Vol. 286, Issue 24
  • DOI: 10.1074/jbc.M110.216804

Isoprenyl diphosphate synthases: the chain length determining step in terpene biosynthesis
journal, November 2018

Characterization of CYP76M5–8 Indicates Metabolic Plasticity within a Plant Biosynthetic Gene Cluster
journal, January 2012

  • Wang, Qiang; Hillwig, Matthew L.; Okada, Kazunori
  • Journal of Biological Chemistry, Vol. 287, Issue 9
  • DOI: 10.1074/jbc.M111.305599

Cross-talk between the Cytosolic Mevalonate and the Plastidial Methylerythritol Phosphate Pathways in Tobacco Bright Yellow-2 Cells
journal, May 2003

  • Hemmerlin, Andréa; Hoeffler, Jean-François; Meyer, Odile
  • Journal of Biological Chemistry, Vol. 278, Issue 29
  • DOI: 10.1074/jbc.M302526200

Promiscuous terpene synthases from Prunella vulgaris highlight the importance of substrate and compartment switching in terpene synthase evolution
journal, April 2019

  • Johnson, Sean R.; Bhat, Wajid Waheed; Sadre, Radin
  • New Phytologist, Vol. 223, Issue 1
  • DOI: 10.1111/nph.15778

Product Rearrangement from Altering a Single Residue in the Rice syn -Copalyl Diphosphate Synthase
journal, February 2016

Identification of Diterpene Biosynthetic Gene Clusters and Functional Analysis of Labdane-Related Diterpene Cyclases in Phomopsis amygdali
journal, April 2008

  • Toyomasu, Tomonobu; Niida, Rie; Kenmoku, Hiromichi
  • Bioscience, Biotechnology, and Biochemistry, Vol. 72, Issue 4
  • DOI: 10.1271/bbb.70790

A Single Residue Switch Converts Abietadiene Synthase into a Pimaradiene Specific Cyclase
journal, December 2007

  • Wilderman, P. Ross; Peters, Reuben J.
  • Journal of the American Chemical Society, Vol. 129, Issue 51
  • DOI: 10.1021/ja074977g

A database-driven approach identifies additional diterpene synthase activities in the mint family (Lamiaceae)
journal, November 2018

  • Johnson, Sean R.; Bhat, Wajid Waheed; Bibik, Jacob
  • Journal of Biological Chemistry, Vol. 294, Issue 4
  • DOI: 10.1074/jbc.RA118.006025

Molecular and functional evolution of the fungal diterpene synthase genes
journal, October 2015

  • Fischer, Marc JC; Rustenhloz, Camille; Leh-Louis, Véronique
  • BMC Microbiology, Vol. 15, Issue 1
  • DOI: 10.1186/s12866-015-0564-8

Structure of limonene synthase, a simple model for terpenoid cyclase catalysis
journal, March 2007

  • Hyatt, D. C.; Youn, B.; Zhao, Y.
  • Proceedings of the National Academy of Sciences, Vol. 104, Issue 13
  • DOI: 10.1073/pnas.0700915104

Structure, mechanism and function of prenyltransferases: Structure, mechanism and function of prenyltransferases
journal, July 2002

Structure of a Three-Domain Sesquiterpene Synthase: A Prospective Target for Advanced Biofuels Production
journal, December 2011

  • McAndrew, Ryan P.; Peralta-Yahya, Pamela P.; DeGiovanni, Andy
  • Structure, Vol. 19, Issue 12
  • DOI: 10.1016/j.str.2011.09.013

Emergence of terpene cyclization in Artemisia annua
journal, February 2015

  • Salmon, Melissa; Laurendon, Caroline; Vardakou, Maria
  • Nature Communications, Vol. 6, Issue 1
  • DOI: 10.1038/ncomms7143

Network Analysis of the MVA and MEP Pathways for Isoprenoid Synthesis
journal, April 2013

Terpenes in Cannabis sativa – From plant genome to humans
journal, July 2019

Functional Characterization of Two Class II Diterpene Synthases Indicates Additional Specialized Diterpenoid Pathways in Maize (Zea mays)
journal, October 2018

Molecular Diversity of Terpene Synthases in the Liverwort Marchantia polymorpha
journal, September 2016

Carnosic acid biosynthesis elucidated by a synthetic biology platform
journal, March 2016

  • Ignea, Codruta; Athanasakoglou, Anastasia; Ioannou, Efstathia
  • Proceedings of the National Academy of Sciences, Vol. 113, Issue 13
  • DOI: 10.1073/pnas.1523787113

Unknown components of the plastidial permeome
journal, August 2014

Molecular cloning, expression and characterization of cDNA encoding cis-prenyltransferases from Hevea brasiliensis: A key factor participating in natural rubber biosynthesis
journal, November 2003

  • Asawatreratanakul, Kasem; Zhang, Yuan-Wei; Wititsuwannakul, Dhirayos
  • European Journal of Biochemistry, Vol. 270, Issue 23
  • DOI: 10.1046/j.1432-1033.2003.03863.x

Functional plasticity of paralogous diterpene synthases involved in conifer defense
journal, January 2008

  • Keeling, C. I.; Weisshaar, S.; Lin, R. P. C.
  • Proceedings of the National Academy of Sciences, Vol. 105, Issue 3
  • DOI: 10.1073/pnas.0709466105

P450s controlling metabolic bifurcations in plant terpene specialized metabolism
journal, September 2017

cis or trans with class II diterpene cyclases
journal, January 2017

  • Jia, Meirong; Peters, Reuben J.
  • Organic & Biomolecular Chemistry, Vol. 15, Issue 15
  • DOI: 10.1039/C7OB00510E

The Gymnosperm Cytochrome P450 CYP750B1 Catalyzes Stereospecific Monoterpene Hydroxylation of (+)-Sabinene in Thujone Biosynthesis in Western Redcedar
journal, March 2015

  • Gesell, Andreas; Blaukopf, Markus; Madilao, Lina
  • Plant Physiology, Vol. 168, Issue 1
  • DOI: 10.1104/pp.15.00315

Predicting pathways for terpene formation from first principles – routes to known and new sesquiterpenes
journal, January 2014

  • Isegawa, Miho; Maeda, Satoshi; Tantillo, Dean J.
  • Chemical Science, Vol. 5, Issue 4
  • DOI: 10.1039/c3sc53293c

Biosynthesis of the Diterpenoid Lycosantalonol via Nerylneryl Diphosphate in Solanum lycopersicum
journal, March 2015

Structure and Mechanism of an Arabidopsis Medium/Long-Chain-Length Prenyl Pyrophosphate Synthase
journal, January 2011

  • Hsieh, Fu-Lien; Chang, Tao-Hsin; Ko, Tzu-Ping
  • Plant Physiology, Vol. 155, Issue 3
  • DOI: 10.1104/pp.110.168799

Predicting the Functions and Specificity of Triterpenoid Synthases: A Mechanism-Based Multi-intermediate Docking Approach
journal, October 2014

Diterpene cyclases and the nature of the isoprene fold
journal, April 2010

  • Cao, Rong; Zhang, Yonghui; Mann, Francis M.
  • Proteins: Structure, Function, and Bioinformatics, Vol. 78, Issue 11
  • DOI: 10.1002/prot.22751

Arabidopsis thaliana isoprenyl diphosphate synthases produce the C 25 intermediate geranylfarnesyl diphosphate
journal, December 2015

  • Nagel, Raimund; Bernholz, Carolin; Vranová, Eva
  • The Plant Journal, Vol. 84, Issue 5
  • DOI: 10.1111/tpj.13064

Two rings in them all: The labdane-related diterpenoids
journal, January 2010

One amino acid makes the difference: the formation of ent-kaurene and 16α-hydroxy-ent-kaurane by diterpene synthases in poplar
journal, October 2015

The formation and function of plant volatiles: perfumes for pollinator attraction and defense
journal, June 2002

Correction to Structural and Chemical Biology of Terpenoid Cyclases
journal, December 2018

The early stages of taxol biosynthesis: An interim report on the synthesis and identification of early pathway metabolites
journal, January 2012

  • Guerra-Bubb, Jennifer; Croteau, Rodney; Williams, Robert M.
  • Natural Product Reports, Vol. 29, Issue 6
  • DOI: 10.1039/c2np20021j

Cyclopentane-forming di/sesterterpene synthases: widely distributed enzymes in bacteria, fungi, and plants
journal, January 2018

  • Minami, Atsushi; Ozaki, Taro; Liu, Chengwei
  • Natural Product Reports, Vol. 35, Issue 12
  • DOI: 10.1039/C8NP00026C

Functional Characterization of Nine Norway Spruce TPS Genes and Evolution of Gymnosperm Terpene Synthases of the TPS-d Subfamily
journal, August 2004

  • Martin, Diane M.; Fäldt, Jenny; Bohlmann, Jörg
  • Plant Physiology, Vol. 135, Issue 4
  • DOI: 10.1104/pp.104.042028

Slow-Starter Enzymes: Role of Active-Site Architecture in the Catalytic Control of the Biosynthesis of Taxadiene by Taxadiene Synthase
journal, May 2018

Cytosolic monoterpene biosynthesis is supported by plastid-generated geranyl diphosphate substrate in transgenic tomato fruits
journal, May 2013

  • Gutensohn, Michael; Orlova, Irina; Nguyen, Thuong T. H.
  • The Plant Journal, Vol. 75, Issue 3
  • DOI: 10.1111/tpj.12212

A Single Residue Switch for Mg 2+ -dependent Inhibition Characterizes Plant Class II Diterpene Cyclases from Primary and Secondary Metabolism
journal, April 2010

  • Mann, Francis M.; Prisic, Sladjana; Davenport, Emily K.
  • Journal of Biological Chemistry, Vol. 285, Issue 27
  • DOI: 10.1074/jbc.M110.123307

CYP701A8: A Rice ent -Kaurene Oxidase Paralog Diverted to More Specialized Diterpenoid Metabolism
journal, January 2012

  • Wang, Qiang; Hillwig, Matthew L.; Wu, Yisheng
  • Plant Physiology, Vol. 158, Issue 3
  • DOI: 10.1104/pp.111.187518

Plant diterpene synthases: exploring modularity and metabolic diversity for bioengineering
journal, July 2015

Biosynthesis of the psychotropic plant diterpene salvinorin A: Discovery and characterization of the Salvia divinorum clerodienyl diphosphate synthase
journal, February 2017

  • Pelot, Kyle A.; Mitchell, Rod; Kwon, Moonhyuk
  • The Plant Journal, Vol. 89, Issue 5
  • DOI: 10.1111/tpj.13427

Cloning of a Full-length cDNA Encoding ent -Kaurene Synthase from Gibberella fujikuroi : Functional Analysis of a Bifunctional Diterpene Cyclase
journal, January 2000

  • Toyomasu, Tomonobu; Kawaide, Hiroshi; Ishizaki, Atsuko
  • Bioscience, Biotechnology, and Biochemistry, Vol. 64, Issue 3
  • DOI: 10.1271/bbb.64.660

The MutT Proteins or “Nudix” Hydrolases, a Family of Versatile, Widely Distributed, “Housecleaning” Enzymes
journal, October 1996

  • Bessman, Maurice J.; Frick, David N.; O'Handley, Suzanne F.
  • Journal of Biological Chemistry, Vol. 271, Issue 41
  • DOI: 10.1074/jbc.271.41.25059

Microbial engineering for the production of advanced biofuels
journal, August 2012

  • Peralta-Yahya, Pamela P.; Zhang, Fuzhong; del Cardayre, Stephen B.
  • Nature, Vol. 488, Issue 7411
  • DOI: 10.1038/nature11478

A Novel Pathway for Sesquiterpene Biosynthesis from Z,Z -Farnesyl Pyrophosphate in the Wild Tomato Solanum habrochaites
journal, January 2009

  • Sallaud, Christophe; Rontein, Denis; Onillon, Sandrine
  • The Plant Cell, Vol. 21, Issue 1
  • DOI: 10.1105/tpc.107.057885

Expanding the Landscape of Diterpene Structural Diversity through Stereochemically Controlled Combinatorial Biosynthesis
journal, January 2016

  • Andersen-Ranberg, Johan; Kongstad, Kenneth Thermann; Nielsen, Morten Thrane
  • Angewandte Chemie International Edition, Vol. 55, Issue 6
  • DOI: 10.1002/anie.201510650

Discovery of a metabolic alternative to the classical mevalonate pathway
journal, December 2013

A P450-centric view of plant evolution: P450-centric evolution
journal, March 2011

Biochemical and Molecular Genetic Aspects of Floral Scents
journal, March 2000

Structure, function and inhibition of ent-kaurene synthase from Bradyrhizobium japonicum
journal, October 2014

  • Liu, Wenting; Feng, Xinxin; Zheng, Yingying
  • Scientific Reports, Vol. 4, Issue 1
  • DOI: 10.1038/srep06214

Functional diversity of 2-oxoglutarate/Fe(II)-dependent dioxygenases in plant metabolism
journal, October 2014

Gibberellin biosynthesis in bacteria: Separate ent -copalyl diphosphate and ent -kaurene synthases in Bradyrhizobium japonicum
journal, December 2008

A Third Class: Functional Gibberellin Biosynthetic Operon in Beta-Proteobacteria
journal, November 2018

  • Nagel, Raimund; Bieber, John E.; Schmidt-Dannert, Mark G.
  • Frontiers in Microbiology, Vol. 9
  • DOI: 10.3389/fmicb.2018.02916

Hedycaryol Synthase in Complex with Nerolidol Reveals Terpene Cyclase Mechanism
journal, January 2014

  • Baer, Philipp; Rabe, Patrick; Citron, Christian A.
  • ChemBioChem, Vol. 15, Issue 2
  • DOI: 10.1002/cbic.201300708

Diterpene synthases of the biosynthetic system of medicinally active diterpenoids in Marrubium vulgare
journal, July 2014

  • Zerbe, Philipp; Chiang, Angela; Dullat, Harpreet
  • The Plant Journal, Vol. 79, Issue 6
  • DOI: 10.1111/tpj.12589

Molecular Cloning, Expression, and Functional Analysis of a cis -Prenyltransferase from Arabidopsis thaliana : IMPLICATIONS IN RUBBER BIOSYNTHESIS
journal, April 2000

  • Oh, Soo Kyung; Han, Kyung Hwan; Ryu, Stephen B.
  • Journal of Biological Chemistry, Vol. 275, Issue 24
  • DOI: 10.1074/jbc.M002000200

Plant P450s as versatile drivers for evolution of species-specific chemical diversity
journal, February 2013

  • Hamberger, Björn; Bak, Søren
  • Philosophical Transactions of the Royal Society B: Biological Sciences, Vol. 368, Issue 1612
  • DOI: 10.1098/rstb.2012.0426

De novo formation of an aggregation pheromone precursor by an isoprenyl diphosphate synthase-related terpene synthase in the harlequin bug
journal, August 2018

  • Lancaster, Jason; Khrimian, Ashot; Young, Sharon
  • Proceedings of the National Academy of Sciences, Vol. 115, Issue 37
  • DOI: 10.1073/pnas.1800008115

Isoprenoid biosynthesis in Archaea – Biochemical and evolutionary implications
journal, January 2011

  • Matsumi, Rie; Atomi, Haruyuki; Driessen, Arnold J. M.
  • Research in Microbiology, Vol. 162, Issue 1, p. 39-52
  • DOI: 10.1016/j.resmic.2010.10.003

Biosynthesis of the oxygenated diterpene nezukol in the medicinal plant Isodon rubescens is catalyzed by a pair of diterpene synthases
journal, April 2017

From The Cover: The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers
journal, January 2005

  • Dudareva, N.; Andersson, S.; Orlova, I.
  • Proceedings of the National Academy of Sciences, Vol. 102, Issue 3
  • DOI: 10.1073/pnas.0407360102

Computational-guided discovery and characterization of a sesquiterpene synthase from Streptomyces clavuligerus
journal, April 2015

  • Chow, Jeng-Yeong; Tian, Bo-Xue; Ramamoorthy, Gurusankar
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 18
  • DOI: 10.1073/pnas.1505127112

Identification of amino acid networks governing catalysis in the closed complex of class I terpene synthases
journal, February 2016

  • Schrepfer, Patrick; Buettner, Alexander; Goerner, Christian
  • Proceedings of the National Academy of Sciences, Vol. 113, Issue 8
  • DOI: 10.1073/pnas.1519680113

A Tandem Array of ent -Kaurene Synthases in Maize with Roles in Gibberellin and More Specialized Metabolism
journal, November 2015

Biosynthesis, elicitation and roles of monocot terpenoid phytoalexins
journal, March 2014

  • Schmelz, Eric A.; Huffaker, Alisa; Sims, James W.
  • The Plant Journal, Vol. 79, Issue 4
  • DOI: 10.1111/tpj.12436

Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential
journal, February 2006

Contribution of isopentenyl phosphate to plant terpenoid metabolism
journal, August 2018

Terpenoid Synthases—From Chemical Ecology and Forest Fires to Biofuels and Bioproducts
journal, December 2011

The essence of being extremophilic: the role of the unique archaeal membrane lipids
journal, August 1998

  • van de Vossenberg, Jack L. C. M.; Driessen, Arnold J. M.; Konings, W. N.
  • Extremophiles, Vol. 2, Issue 3
  • DOI: 10.1007/s007920050056

Plant diterpenoid metabolism for manufacturing the biopharmaceuticals of tomorrow: prospects and challenges
journal, May 2017

The terpene synthase gene family in Tripterygium wilfordii harbors a labdane-type diterpene synthase among the monoterpene synthase TPS-b subfamily
journal, February 2017

  • Hansen, Nikolaj L.; Heskes, Allison M.; Hamberger, Britta
  • The Plant Journal, Vol. 89, Issue 3
  • DOI: 10.1111/tpj.13410

Plasticity and Evolution of (+)-3-Carene Synthase and (−)-Sabinene Synthase Functions of a Sitka Spruce Monoterpene Synthase Gene Family Associated with Weevil Resistance
journal, July 2014

  • Roach, Christopher R.; Hall, Dawn E.; Zerbe, Philipp
  • Journal of Biological Chemistry, Vol. 289, Issue 34
  • DOI: 10.1074/jbc.M114.571703

Formation of Monoterpenes in Antirrhinum majus and Clarkia breweri Flowers Involves Heterodimeric Geranyl Diphosphate Synthases
journal, March 2004

  • Tholl, Dorothea; Kish, Christine M.; Orlova, Irina
  • The Plant Cell, Vol. 16, Issue 4
  • DOI: 10.1105/tpc.020156

Nonlinear partial differential equations and applications: Bornyl diphosphate synthase: Structure and strategy for carbocation manipulation by a terpenoid cyclase
journal, November 2002

  • Whittington, D. A.; Wise, M. L.; Urbansky, M.
  • Proceedings of the National Academy of Sciences, Vol. 99, Issue 24
  • DOI: 10.1073/pnas.232591099

CYP76M7 Is an ent -Cassadiene C11α-Hydroxylase Defining a Second Multifunctional Diterpenoid Biosynthetic Gene Cluster in Rice
journal, October 2009

  • Swaminathan, Sivakumar; Morrone, Dana; Wang, Qiang
  • The Plant Cell, Vol. 21, Issue 10
  • DOI: 10.1105/tpc.108.063677

A Novel Labda-7,13E-dien-15-ol-Producing Bifunctional Diterpene Synthase from Selaginella moellendorffii
journal, July 2011

  • Mafu, Sibongile; Hillwig, Matthew L.; Peters, Reuben J.
  • ChemBioChem, Vol. 12, Issue 13
  • DOI: 10.1002/cbic.201100336

CYP725A4 from Yew Catalyzes Complex Structural Rearrangement of Taxa-4(5),11(12)-diene into the Cyclic Ether 5(12)-Oxa-3(11)-cyclotaxane
journal, December 2007

  • Rontein, Denis; Onillon, Sandrine; Herbette, Gaëtan
  • Journal of Biological Chemistry, Vol. 283, Issue 10
  • DOI: 10.1074/jbc.M708950200

Crystal Structure of Human Squalene Synthase: A KEY ENZYME IN CHOLESTEROL BIOSYNTHESIS
journal, July 2000

  • Pandit, Jayvardhan; Danley, Dennis E.; Schulte, Gayle K.
  • Journal of Biological Chemistry, Vol. 275, Issue 39
  • DOI: 10.1074/jbc.M004132200

Functional characterization of the rice kaurene synthase-like gene family
journal, February 2007

Total biosynthesis of the cyclic AMP booster forskolin from Coleus forskohlii
journal, March 2017

  • Pateraki, Irini; Andersen-Ranberg, Johan; Jensen, Niels Bjerg
  • eLife, Vol. 6
  • DOI: 10.7554/eLife.23001

Substitution of Two Active-Site Residues Alters C9-Hydroxylation in a Class II Diterpene Synthase
journal, October 2016

  • Mafu, Sibongile; Fischer, Emil; Addison, J. Bennett
  • ChemBioChem, Vol. 17, Issue 24
  • DOI: 10.1002/cbic.201600419

The Application of Synthetic Biology to Elucidation of Plant Mono-, Sesqui-, and Diterpenoid Metabolism
journal, January 2015

The terpenoid theory of the origin of cellular life: the evolution of terpenoids to cholesterol
journal, September 1994

Probing the Role of the DXDD Motif in Class II Diterpene Cyclases
journal, May 2007

Terpene synthases and the regulation, diversity and biological roles of terpene metabolism
journal, June 2006

Production of Bioactive Diterpenoids in the Euphorbiaceae Depends on Evolutionarily Conserved Gene Clusters
journal, August 2014

  • King, Andrew J.; Brown, Geoffrey D.; Gilday, Alison D.
  • The Plant Cell, Vol. 26, Issue 8
  • DOI: 10.1105/tpc.114.129668

Abietadiene Synthase from Grand Fir ( Abies grandis ):  Characterization and Mechanism of Action of the “Pseudomature” Recombinant Enzyme †
journal, December 2000

  • Peters, Reuben J.; Flory, Janice E.; Jetter, Reinhard
  • Biochemistry, Vol. 39, Issue 50
  • DOI: 10.1021/bi001997l

Genome-wide identification and characterization of novel genes involved in terpenoid biosynthesis in Salvia miltiorrhiza
journal, January 2012

  • Ma, Yimian; Yuan, Lichai; Wu, Bin
  • Journal of Experimental Botany, Vol. 63, Issue 7
  • DOI: 10.1093/jxb/err466

Two residues determine the product profile of the class II diterpene synthases TPS14 and TPS21 of Tripterygium wilfordii
journal, June 2017

Insights into Diterpene Cyclization from Structure of Bifunctional Abietadiene Synthase from Abies grandis
journal, January 2012

  • Zhou, Ke; Gao, Yang; Hoy, Julie A.
  • Journal of Biological Chemistry, Vol. 287, Issue 9
  • DOI: 10.1074/jbc.M111.337592

Towards a comprehensive understanding of the structural dynamics of a bacterial diterpene synthase during catalysis
journal, September 2018

Blocking Deprotonation with Retention of Aromaticity in a Plant ent -Copalyl Diphosphate Synthase Leads to Product Rearrangement
journal, November 2015

  • Potter, Kevin C.; Zi, Jiachen; Hong, Young J.
  • Angewandte Chemie International Edition, Vol. 55, Issue 2
  • DOI: 10.1002/anie.201509060

Crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis in Arabidopsis thaliana
journal, May 2003

  • Laule, O.; Furholz, A.; Chang, H. -S.
  • Proceedings of the National Academy of Sciences, Vol. 100, Issue 11
  • DOI: 10.1073/pnas.1031755100

The function of terpene natural products in the natural world
journal, June 2007

Unearthing a sesterterpene biosynthetic repertoire in the Brassicaceae through genome mining reveals convergent evolution
journal, July 2017

  • Huang, Ancheng C.; Kautsar, Satria A.; Hong, Young J.
  • Proceedings of the National Academy of Sciences, Vol. 114, Issue 29
  • DOI: 10.1073/pnas.1705567114

The Primary Diterpene Synthase Products of Picea abies Levopimaradiene/Abietadiene Synthase (PaLAS) Are Epimers of a Thermally Unstable Diterpenol
journal, April 2011

  • Keeling, Christopher I.; Madilao, Lina L.; Zerbe, Philipp
  • Journal of Biological Chemistry, Vol. 286, Issue 24
  • DOI: 10.1074/jbc.M111.245951

Microbial-type terpene synthase genes occur widely in nonseed land plants, but not in seed plants
journal, October 2016

  • Jia, Qidong; Li, Guanglin; Köllner, Tobias G.
  • Proceedings of the National Academy of Sciences, Vol. 113, Issue 43
  • DOI: 10.1073/pnas.1607973113

Terpenoid biomaterials
journal, May 2008

An annotated transcriptome of highly inbred Thuja plicata (Cupressaceae) and its utility for gene discovery of terpenoid biosynthesis and conifer defense
journal, April 2018

  • Shalev, Tal J.; Yuen, Macaire M. S.; Gesell, Andreas
  • Tree Genetics & Genomes, Vol. 14, Issue 3
  • DOI: 10.1007/s11295-018-1248-y

Functional Diversity of Diterpene Synthases in the Biofuel Crop Switchgrass
journal, July 2018

  • Pelot, Kyle A.; Chen, Ruibing; Hagelthorn, David M.
  • Plant Physiology, Vol. 178, Issue 1
  • DOI: 10.1104/pp.18.00590

Unusual P450 reactions in plant secondary metabolism
journal, March 2011

  • Mizutani, Masaharu; Sato, Fumihiko
  • Archives of Biochemistry and Biophysics, Vol. 507, Issue 1
  • DOI: 10.1016/j.abb.2010.09.026

Gibberellin Biosynthetic Pathway in Gibberella fujikuroi: Evidence for a Gene Cluster
journal, December 1998

  • Tudzynski, Bettina; Hölter, Katja
  • Fungal Genetics and Biology, Vol. 25, Issue 3, p. 157-170
  • DOI: 10.1006/fgbi.1998.1095

Cloning and Characterization of Ginkgo biloba Levopimaradiene Synthase, Which Catalyzes the First Committed Step in Ginkgolide Biosynthesis
journal, August 2001

  • Schepmann, Hala G.; Pang, Jihai; Matsuda, Seiichi P. T.
  • Archives of Biochemistry and Biophysics, Vol. 392, Issue 2
  • DOI: 10.1006/abbi.2001.2438

Allelopathic potential of Tagetes minuta terpenes by a chemical, anatomical and phytotoxic approach
journal, December 2008

  • López, M. Liza; Bonzani, Norma E.; Zygadlo, Julio A.
  • Biochemical Systematics and Ecology, Vol. 36, Issue 12
  • DOI: 10.1016/j.bse.2008.11.003

Biosynthesis via carbocations: Theoretical studies on terpene formation
journal, January 2011

A (–)-kolavenyl diphosphate synthase catalyzes the first step of salvinorin A biosynthesis in Salvia divinorum
journal, February 2017

  • Chen, Xiaoyue; Berim, Anna; Dayan, Franck E.
  • Journal of Experimental Botany, Vol. 68, Issue 5
  • DOI: 10.1093/jxb/erw493

Toward a Biosynthetic Route to Sclareol and Amber Odorants
journal, November 2012

  • Schalk, Michel; Pastore, Laurence; Mirata, Marco A.
  • Journal of the American Chemical Society, Vol. 134, Issue 46
  • DOI: 10.1021/ja307404u

Improving peppermint essential oil yield and composition by metabolic engineering
journal, September 2011

  • Lange, B. M.; Mahmoud, S. S.; Wildung, M. R.
  • Proceedings of the National Academy of Sciences, Vol. 108, Issue 41
  • DOI: 10.1073/pnas.1111558108

Trichome specific expression of the tobacco (Nicotiana sylvestris) cembratrien-ol synthase genes is controlled by both activating and repressing cis-regions
journal, May 2010

  • Ennajdaoui, Hanane; Vachon, Gilles; Giacalone, Cécile
  • Plant Molecular Biology, Vol. 73, Issue 6
  • DOI: 10.1007/s11103-010-9648-x

MTPSLs: New Terpene Synthases in Nonseed Plants
journal, February 2018

Bacterial diterpene synthases: new opportunities for mechanistic enzymology and engineered biosynthesis
journal, April 2012

  • Smanski, Michael J.; Peterson, Ryan M.; Huang, Sheng-Xiong
  • Current Opinion in Chemical Biology, Vol. 16, Issue 1-2
  • DOI: 10.1016/j.cbpa.2012.03.002

Enzymatic 13 C Labeling and Multidimensional NMR Analysis of Miltiradiene Synthesized by Bifunctional Diterpene Cyclase in Selaginella moellendorffii
journal, October 2011

  • Sugai, Yoshinori; Ueno, Yohei; Hayashi, Ken-ichiro
  • Journal of Biological Chemistry, Vol. 286, Issue 50
  • DOI: 10.1074/jbc.M111.302703

Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450 monooxygenase
journal, May 2005

  • Ro, D. -K.; Arimura, G. -I.; Lau, S. Y. W.
  • Proceedings of the National Academy of Sciences, Vol. 102, Issue 22
  • DOI: 10.1073/pnas.0500825102

The carbocation continuum in terpene biosynthesis—where are the secondary cations?
journal, January 2010

  • Tantillo, Dean J.
  • Chemical Society Reviews, Vol. 39, Issue 8
  • DOI: 10.1039/b917107j

Novel Product Chemistry from Mechanistic Analysis of ent -Copalyl Diphosphate Synthases from Plant Hormone Biosynthesis
journal, May 2014

  • Potter, Kevin; Criswell, Jared; Zi, Jiachen
  • Angewandte Chemie International Edition, Vol. 53, Issue 28
  • DOI: 10.1002/anie.201402911

Gene Discovery of Modular Diterpene Metabolism in Nonmodel Systems
journal, April 2013

  • Zerbe, Philipp; Hamberger, Björn; Yuen, Macaire M. S.
  • Plant Physiology, Vol. 162, Issue 2
  • DOI: 10.1104/pp.113.218347

Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis
journal, September 2016

Synthesizing specificity: multiple approaches to understanding the attack and defense of plants
journal, May 2012

Discovery, Biosynthesis and Stress-Related Accumulation of Dolabradiene-Derived Defenses in Maize
journal, February 2018

  • Mafu, Sibongile; Ding, Yezhang; Murphy, Katherine M.
  • Plant Physiology, Vol. 176, Issue 4
  • DOI: 10.1104/pp.17.01351

Investigating the Phylogenetic Range of Gibberellin Biosynthesis in Bacteria
journal, April 2017

Monoterpenes in the glandular trichomes of tomato are synthesized from a neryl diphosphate precursor rather than geranyl diphosphate
journal, June 2009

  • Schilmiller, A. L.; Schauvinhold, I.; Larson, M.
  • Proceedings of the National Academy of Sciences, Vol. 106, Issue 26
  • DOI: 10.1073/pnas.0904113106

Crystal structure of CYP76AH1 in 4-PI-bound state from Salvia miltiorrhiza
journal, April 2019

  • Gu, Mingyue; Wang, Mingzhu; Guo, Juan
  • Biochemical and Biophysical Research Communications, Vol. 511, Issue 4
  • DOI: 10.1016/j.bbrc.2019.02.103

Traversing the fungal terpenome
journal, January 2014

  • Quin, Maureen B.; Flynn, Christopher M.; Schmidt-Dannert, Claudia
  • Nat. Prod. Rep., Vol. 31, Issue 10
  • DOI: 10.1039/C4NP00075G

Biotechnological production of natural zero-calorie sweeteners
journal, April 2014

A Lettuce ( Lactuca sativa ) Homolog of Human Nogo-B Receptor Interacts with cis -Prenyltransferase and Is Necessary for Natural Rubber Biosynthesis
journal, December 2014

  • Qu, Yang; Chakrabarty, Romit; Tran, Hue T.
  • Journal of Biological Chemistry, Vol. 290, Issue 4
  • DOI: 10.1074/jbc.M114.616920

X-ray Crystallographic Studies of Substrate Binding to Aristolochene Synthase Suggest a Metal Ion Binding Sequence for Catalysis
journal, April 2008

  • Shishova, Ekaterina Y.; Yu, Fanglei; Miller, David J.
  • Journal of Biological Chemistry, Vol. 283, Issue 22
  • DOI: 10.1074/jbc.M800659200

A raison d’être for two distinct pathways in the early steps of plant isoprenoid biosynthesis?
journal, April 2012

Cloning of casbene and neocembrene synthases from Euphorbiaceae plants and expression in Saccharomyces cerevisiae
journal, September 2010

Cytochrome P450 enzymes: A driving force of plant diterpene diversity
journal, May 2019

The tomato cis- prenyltransferase gene family
journal, December 2012

  • Akhtar, Tariq A.; Matsuba, Yuki; Schauvinhold, Ines
  • The Plant Journal, Vol. 73, Issue 4
  • DOI: 10.1111/tpj.12063

Diterpene Synthase‐Catalyzed Biosynthesis of Distinct Clerodane Stereoisomers
journal, November 2018

  • Pelot, Kyle A.; Hagelthorn, David M.; Hong, Young J.
  • ChemBioChem, Vol. 20, Issue 1
  • DOI: 10.1002/cbic.201800580

A Pair of Residues That Interactively Affect Diterpene Synthase Product Outcome
journal, February 2017

Characterization of the kaurene oxidase CYP701A3, a multifunctional cytochrome P450 from gibberellin biosynthesis
journal, October 2010

  • Morrone, Dana; Chen, Xiaoming; Coates, Robert M.
  • Biochemical Journal, Vol. 431, Issue 3
  • DOI: 10.1042/BJ20100597

Geranyl diphosphate synthase: Cloning, expression, and characterization of this prenyltransferase as a heterodimer
journal, November 1999

  • Burke, C. C.; Wildung, M. R.; Croteau, R.
  • Proceedings of the National Academy of Sciences, Vol. 96, Issue 23
  • DOI: 10.1073/pnas.96.23.13062

Origins and Early Evolution of the Mevalonate Pathway of Isoprenoid Biosynthesis in the Three Domains of Life
journal, July 2010

Uptake of isopentenyl diphosphate by plastids isolated from Vitis vinifera L. cell suspensions
journal, August 1993

  • Soler, E.; Clastre, M.; Bantignies, B.
  • Planta, Vol. 191, Issue 3
  • DOI: 10.1007/BF00195689

Following evolution's lead to a single residue switch for diterpene synthase product outcome
journal, April 2007

  • Xu, M.; Wilderman, P. R.; Peters, R. J.
  • Proceedings of the National Academy of Sciences, Vol. 104, Issue 18
  • DOI: 10.1073/pnas.0611454104

Parsing a multifunctional biosynthetic gene cluster from rice: Biochemical characterization of CYP71Z6 & 7
journal, October 2011

Gene Networks Underlying Cannabinoid and Terpenoid Accumulation in Cannabis
journal, May 2019

  • Zager, Jordan J.; Lange, Iris; Srividya, Narayanan
  • Plant Physiology, Vol. 180, Issue 4
  • DOI: 10.1104/pp.18.01506

Synthetic biology and the development of tools for metabolic engineering
journal, May 2012

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus
journal, February 2018

  • Heskes, Allison M.; Sundram, Tamil C. M.; Boughton, Berin A.
  • The Plant Journal, Vol. 93, Issue 5
  • DOI: 10.1111/tpj.13822

Crystal Structure of (+)-δ-Cadinene Synthase from Gossypium arboreum and Evolutionary Divergence of Metal Binding Motifs for Catalysis
journal, July 2009

  • Gennadios, Heather A.; Gonzalez, Veronica; Di Costanzo, Luigi
  • Biochemistry, Vol. 48, Issue 26
  • DOI: 10.1021/bi900483b

The chemical logic of plant natural product biosynthesis
journal, June 2014

  • Anarat-Cappillino, Gülbenk; Sattely, Elizabeth S.
  • Current Opinion in Plant Biology, Vol. 19
  • DOI: 10.1016/j.pbi.2014.03.007

Identification and functional analysis of bifunctional ent -kaurene synthase from the moss Physcomitrella patens
journal, October 2006

Changing Face: A Key Residue for the Addition of Water by Sclareol Synthase
journal, March 2018

Characterization of CYP71Z18 indicates a role in maize zealexin biosynthesis
journal, January 2016

1.55Å-resolution structure of ent-copalyl diphosphate synthase and exploration of general acid function by site-directed mutagenesis
journal, January 2014

  • Köksal, Mustafa; Potter, Kevin; Peters, Reuben J.
  • Biochimica et Biophysica Acta (BBA) - General Subjects, Vol. 1840, Issue 1
  • DOI: 10.1016/j.bbagen.2013.09.004

Oxidation and cyclization of casbene in the biosynthesis of Euphorbia factors from mature seeds of Euphorbia lathyris L.
journal, August 2016

  • Luo, Dan; Callari, Roberta; Hamberger, Britta
  • Proceedings of the National Academy of Sciences, Vol. 113, Issue 34
  • DOI: 10.1073/pnas.1607504113

Efficient heterocyclisation by (di)terpene synthases
journal, January 2015

  • Mafu, S.; Potter, K. C.; Hillwig, M. L.
  • Chemical Communications, Vol. 51, Issue 70
  • DOI: 10.1039/C5CC05754J

A Single Residue Change Leads to a Hydroxylated Product from the Class II Diterpene Cyclization Catalyzed by Abietadiene Synthase
journal, November 2012

  • Criswell, Jared; Potter, Kevin; Shephard, Freya
  • Organic Letters, Vol. 14, Issue 23
  • DOI: 10.1021/ol3026022

Terpenoid synthase structures: a so far incomplete view of complex catalysis
journal, January 2012

  • Gao, Yang; Honzatko, Richard B.; Peters, Reuben J.
  • Natural Product Reports, Vol. 29, Issue 10
  • DOI: 10.1039/c2np20059g

Elucidation of the biosynthesis of carnosic acid and its reconstitution in yeast
journal, October 2016

  • Scheler, Ulschan; Brandt, Wolfgang; Porzel, Andrea
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms12942

Domain loss has independently occurred multiple times in plant terpene synthase evolution: Complex evolutionary origins for terpene synthases
journal, October 2011

Gibberellin biosynthesis in fungi: genes, enzymes, evolution, and impact on biotechnology
journal, December 2004

Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals
journal, April 2011

  • Morrone, Dana; Hillwig, Matthew L.; Mead, Matthew E.
  • Biochemical Journal, Vol. 435, Issue 3
  • DOI: 10.1042/BJ20101429

Isoprenoid biosynthesis: The evolution of two ancient and distinct pathways across genomes
journal, November 2000

  • Lange, B. M.; Rujan, T.; Martin, W.
  • Proceedings of the National Academy of Sciences, Vol. 97, Issue 24
  • DOI: 10.1073/pnas.240454797

High-level semi-synthetic production of the potent antimalarial artemisinin
journal, April 2013

  • Paddon, C. J.; Westfall, P. J.; Pitera, D. J.
  • Nature, Vol. 496, Issue 7446
  • DOI: 10.1038/nature12051

Catalytic Bases and Stereocontrol in Lamiaceae Class II Diterpene Cyclases
journal, May 2018

Evolution of Diterpene Metabolism: Sitka Spruce CYP720B4 Catalyzes Multiple Oxidations in Resin Acid Biosynthesis of Conifer Defense against Insects
journal, October 2011

  • Hamberger, Björn; Ohnishi, Toshiyuki; Hamberger, Britta
  • Plant Physiology, Vol. 157, Issue 4
  • DOI: 10.1104/pp.111.185843

Terpenoid biosynthesis in trichomes-current status and future opportunities
journal, September 2012

Functional analysis of (4 S )-limonene synthase mutants reveals determinants of catalytic outcome in a model monoterpene synthase
journal, March 2015

  • Srividya, Narayanan; Davis, Edward M.; Croteau, Rodney B.
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 11
  • DOI: 10.1073/pnas.1501203112

Biosynthesis of Sandalwood Oil: Santalum album CYP76F Cytochromes P450 Produce Santalols and Bergamotol
journal, September 2013

Transport of Isoprenoid Intermediates Across Chloroplast Envelope Membranes
journal, January 2005

Diversity, regulation, and evolution of the gibberellin biosynthetic pathway in fungi compared to plants and bacteria
journal, October 2009

Unearthing the roots of the terpenome
journal, April 2008

CYP76AH1 catalyzes turnover of miltiradiene in tanshinones biosynthesis and enables heterologous production of ferruginol in yeasts
journal, June 2013

  • Guo, J.; Zhou, Y. J.; Hillwig, M. L.
  • Proceedings of the National Academy of Sciences, Vol. 110, Issue 29
  • DOI: 10.1073/pnas.1218061110

Diterpene resin acids in conifers
journal, November 2006

Cloning of casbene synthase cDNA: evidence for conserved structural features among terpenoid cyclases in plants.
journal, August 1994

  • Mau, C. J.; West, C. A.
  • Proceedings of the National Academy of Sciences, Vol. 91, Issue 18
  • DOI: 10.1073/pnas.91.18.8497

Integrative analysis of transcript and metabolite profiling data sets to evaluate the regulation of biochemical pathways during photomorphogenesis
journal, April 2006

  • Ghassemian, Majid; Lutes, Jason; Tepperman, James M.
  • Archives of Biochemistry and Biophysics, Vol. 448, Issue 1-2
  • DOI: 10.1016/j.abb.2005.11.020

Combining metabolomics and transcriptomics to characterize tanshinone biosynthesis in Salvia miltiorrhiza
journal, January 2014

Metabolic cross-talk between pathways of terpenoid backbone biosynthesis in spike lavender
journal, October 2015

Accumulation of terpenoid phytoalexins in maize roots is associated with drought tolerance: Maize root phytoalexins play a role in drought tolerance
journal, January 2015

  • Vaughan, Martha M.; Christensen, Shawn; Schmelz, Eric A.
  • Plant, Cell & Environment, Vol. 38, Issue 11
  • DOI: 10.1111/pce.12482

Synthetic biology for microbial production of lipid-based biofuels
journal, December 2015

The Gibberellin perception system evolved to regulate a pre-existing GAMYB-mediated system during land plant evolution
journal, September 2011

  • Aya, Koichiro; Hiwatashi, Yuji; Kojima, Mikiko
  • Nature Communications, Vol. 2, Issue 1
  • DOI: 10.1038/ncomms1552

Catalytic control in terpenoid cyclases: multiscale modeling of thermodynamic, kinetic, and dynamic effects
journal, August 2014

  • Major, Dan Thomas; Freud, Yehoshua; Weitman, Michal
  • Current Opinion in Chemical Biology, Vol. 21
  • DOI: 10.1016/j.cbpa.2014.03.010

Biosynthesis of monoterpene scent compounds in roses
journal, July 2015

  • Magnard, Jean-Louis; Roccia, Aymeric; Caissard, Jean-Claude
  • Science, Vol. 349, Issue 6243
  • DOI: 10.1126/science.aab0696

Novel family of terpene synthases evolved from trans -isoprenyl diphosphate synthases in a flea beetle
journal, March 2016

  • Beran, Franziska; Rahfeld, Peter; Luck, Katrin
  • Proceedings of the National Academy of Sciences, Vol. 113, Issue 11
  • DOI: 10.1073/pnas.1523468113

Cloning of a Gene Cluster Responsible for the Biosynthesis of Diterpene Aphidicolin, a Specific Inhibitor of DNA Polymerase α
journal, January 2004

  • Toyomasu, Tomonobu; Nakaminami, Kentaro; Toshima, Hiroaki
  • Bioscience, Biotechnology, and Biochemistry, Vol. 68, Issue 1
  • DOI: 10.1271/bbb.68.146

Comprehensive Analysis of Cytosolic Nudix Hydrolases in Arabidopsis thaliana
journal, May 2005

  • Ogawa, Takahisa; Ueda, Yayoi; Yoshimura, Kazuya
  • Journal of Biological Chemistry, Vol. 280, Issue 26
  • DOI: 10.1074/jbc.M503536200

Defining the Product Chemical Space of Monoterpenoid Synthases
journal, August 2016

A Red Algal Bourbonane Sesquiterpene Synthase Defined by Microgram-Scale NMR-Coupled Crystalline Sponge X-ray Diffraction Analysis
journal, November 2017

  • Kersten, Roland D.; Lee, Shoukou; Fujita, Daishi
  • Journal of the American Chemical Society, Vol. 139, Issue 46
  • DOI: 10.1021/jacs.7b09452

The Role of Momilactones in Rice Allelopathy
journal, February 2013

Terpene Biosynthesis in Red Algae Is Catalyzed by Microbial Type But Not Typical Plant Terpene Synthases
journal, December 2018

  • Wei, Guo; Jia, Qidong; Chen, Xinlu
  • Plant Physiology, Vol. 179, Issue 2
  • DOI: 10.1104/pp.18.01413

Glandular Trichomes of Leucosceptrum canum Harbor Defensive Sesterterpenoids
journal, June 2010

  • Luo, Shi-Hong; Luo, Qian; Niu, Xue-Mei
  • Angewandte Chemie International Edition, Vol. 49, Issue 26
  • DOI: 10.1002/anie.201000449

Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi
journal, February 2007

  • Toyomasu, T.; Tsukahara, M.; Kaneko, A.
  • Proceedings of the National Academy of Sciences, Vol. 104, Issue 9
  • DOI: 10.1073/pnas.0608426104

Nonseed plant Selaginella moellendorffii has both seed plant and microbial types of terpene synthases
journal, August 2012

  • Li, G.; Kollner, T. G.; Yin, Y.
  • Proceedings of the National Academy of Sciences, Vol. 109, Issue 36
  • DOI: 10.1073/pnas.1204300109

Bifunctional cis -Abienol Synthase from Abies balsamea Discovered by Transcriptome Sequencing and Its Implications for Diterpenoid Fragrance Production
journal, February 2012

  • Zerbe, Philipp; Chiang, Angela; Yuen, Macaire
  • Journal of Biological Chemistry, Vol. 287, Issue 15
  • DOI: 10.1074/jbc.M111.317669

Biosynthesis of the microtubule-destabilizing diterpene pseudolaric acid B from golden larch involves an unusual diterpene synthase
journal, January 2017

  • Mafu, Sibongile; Karunanithi, Prema Sambandaswami; Palazzo, Teresa Ann
  • Proceedings of the National Academy of Sciences, Vol. 114, Issue 5
  • DOI: 10.1073/pnas.1612901114
    Sort by:
    [ × clear filter / sort ]

    Similar Records in DOE PAGES and OSTI.GOV collections: