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Diterpene Synthase-Catalyzed Biosynthesis of Distinct Clerodane Stereoisomers

Journal Article · · ChemBioChem: a European journal of chemical biology
 [1];  [1];  [2];  [2];  [1]
  1. Department of Plant BiologyUniversity of California Davis One Shields Avenue Davis CA 95616 USA
  2. Department of ChemistryUniversity of California Davis One Shields Avenue Davis CA 95616 USA

Not provided.

Research Organization:
Univ. of California, Davis, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
DOE Contract Number:
SC0019178
OSTI ID:
1613140
Journal Information:
ChemBioChem: a European journal of chemical biology, Vol. 20, Issue 1; ISSN 1439-4227
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English

References (64)

A review of salvinorin analogs and their kappa-opioid receptor activity May 2018
Biosynthesis of Lycosantalonol, a cis -Prenyl Derived Diterpenoid November 2014
Neoclerodanes as Atypical Opioid Receptor Ligands: 2012 David W. Robertson Award for Excellence in Medicinal Chemistry April 2013
Salvinorin A Analogs as Probes in Opioid Pharmacology May 2008
Synthesis of Clerodane Diterpenoids and Related Compounds - Stereoselective Construction of the Decalin Skeleton with Multiple Contiguous Stereogenic Centers January 2000
MolDock:  A New Technique for High-Accuracy Molecular Docking June 2006
Ab initio calculation of vibrational circular dichroism spectra using large basis set MP2 force fields July 1994
Anti-inflammatory activities of the methanol extracts and an isolated furanoditerpene constituent of Sphenocentrum jollyanum Pierre (Menispermaceae) March 2006
Identification of a New Diterpene Biosynthetic Gene Cluster that Produces O -Methylkolavelool in Herpetosiphon aurantiacus February 2015
Plant diterpene synthases: exploring modularity and metabolic diversity for bioengineering July 2015
Performance of B3LYP Density Functional Methods for a Large Set of Organic Molecules January 2008
Clerodane diterpenes: sources, structures, and biological activities January 2016
Increasing diterpene yield with a modular metabolic engineering system in E. coli: comparison of MEV and MEP isoprenoid precursor pathway engineering September 2009
The isolation and in vivo Potent Antitumor activity of clerodane diterpenoid from the oleoresin of the brazilian medicinal plant, copaifera langsdorfi desfon. December 1994
Bioassay-guided isolation of a diastereoisomer of kolavenol from Entada abyssinica active on Trypanosoma brucei rhodesiense July 1998
Probing the Role of the DXDD Motif in Class II Diterpene Cyclases May 2007
Biosynthesis of the psychotropic plant diterpene salvinorin A: Discovery and characterization of the Salvia divinorum clerodienyl diphosphate synthase February 2017
Total Synthesis of the Hallucinogenic Neoclerodane Diterpenoid Salvinorin A April 2008
Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus February 2018
Enantioselective Access to Key Intermediates for Salvinorin A and Analogues April 2011
Two residues determine the product profile of the class II diterpene synthases TPS14 and TPS21 of Tripterygium wilfordii June 2017
Clerodane diterpenoids January 1992
A new mixing of Hartree–Fock and local density‐functional theories January 1993
Blocking Deprotonation with Retention of Aromaticity in a Plant ent -Copalyl Diphosphate Synthase Leads to Product Rearrangement November 2015
1.55Å-resolution structure of ent-copalyl diphosphate synthase and exploration of general acid function by site-directed mutagenesis January 2014
Asymmetric Synthesis of Salvinorin A, A Potent κ Opioid Receptor Agonist July 2007
Expanding the Landscape of Diterpene Structural Diversity through Stereochemically Controlled Combinatorial Biosynthesis January 2016
Biosynthesis of heteroscyphic acid A in cell cultures of Heteroscyphus planus: nonequivalent labelling of C-5 units in diterpene biosynthesis January 1995
Product Rearrangement from Altering a Single Residue in the Rice syn -Copalyl Diphosphate Synthase February 2016
The path of chemical reactions - the IRC approach December 1981
Salvinorin A: the ‘magic mint’ hallucinogen finds a molecular target in the kappa opioid receptor March 2003
Catalytic Bases and Stereocontrol in Lamiaceae Class II Diterpene Cyclases May 2018
Anthocyanin attenuates alcohol-induced hepatic injury by inhibiting oxidative stress and proinflammation signaling October 2014
Crispenes F and G, cis -Clerodane Furanoditerpenoids from Tinospora crispa , Inhibit STAT3 Dimerization February 2018
Mechanistic insights into triterpene synthesis from quantum mechanical calculations. Detection of systematic errors in B3LYP cyclization energies January 2006
Salvinorin A: A potent naturally occurring nonnitrogenous   opioid selective agonist August 2002
Biosynthesis of the clerodane furano-diterpene lactone skeleton in Tinospora cordifolia January 1991
Density‐functional thermochemistry. III. The role of exact exchange April 1993
Biosynthesis of the oxygenated diterpene nezukol in the medicinal plant Isodon rubescens is catalyzed by a pair of diterpene synthases April 2017
Functional Diversity of Diterpene Synthases in the Biofuel Crop Switchgrass July 2018
Dynamic Strategic Bond Analysis Yields a Ten-Step Synthesis of 20-nor-Salvinorin A, a Potent κ-OR Agonist November 2017
Reaction path following in mass-weighted internal coordinates July 1990
Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products March 2017
Blocking Deprotonation with Retention of Aromaticity in a Plant ent -Copalyl Diphosphate Synthase Leads to Product Rearrangement November 2015
Cytochromes P450 for Terpene Functionalisation and Metabolic Engineering January 2015
Sesqui- and di-terpene biosynthesis from 13C labelled acetate and mevalonate in cultured cells of Heteroscyphus planus January 1995
Expanding the Landscape of Diterpene Structural Diversity through Stereochemically Controlled Combinatorial Biosynthesis January 2016
Bedeutung der inhärenten Substratreaktivität bei enzymvermittelten Cyclisierungen/Umlagerungen von Carbokationen June 2017
A bitter diterpenoid furanolactone columbin from Calumbae Radix inhibits azoxymethane-induced rat colon carcinogenesis September 2002
Functional Analysis of Eubacterial Diterpene Cyclases Responsible for Biosynthesis of a Diterpene Antibiotic, Terpentecin July 2002
Multi-target mode of action of a Clerodane-type diterpenoid from Polyalthia longifolia targeting African trypanosomes March 2018
Biosynthesis via carbocations: Theoretical studies on terpene formation January 2011
cis or trans with class II diterpene cyclases January 2017
Total Synthesis of (−)-Salvinorin A November 2016
Biosynthesis of the Diterpenoid Lycosantalonol via Nerylneryl Diphosphate in Solanum lycopersicum March 2015
Identification of the Molecular Mechanisms by Which the Diterpenoid Salvinorin A Binds to κ-Opioid Receptors June 2005
Two rings in them all: The labdane-related diterpenoids January 2010
Gene Discovery of Modular Diterpene Metabolism in Nonmodel Systems April 2013
Crispene E, a cis-clerodane diterpene inhibits STAT3 dimerization in breast cancer cells January 2015
Importance of Inherent Substrate Reactivity in Enzyme-Promoted Carbocation Cyclization/Rearrangements June 2017
Second-generation synthesis of salvinorin A June 2009
Clerodane diterpenes: sources, structures, and biological activities January 2016
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density January 1988
Product Rearrangement from Altering a Single Residue in the Rice syn -Copalyl Diphosphate Synthase January 2016