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Evolutionary and Mechanistic Insights from the Reconstruction of α-Humulene Synthases from a Modern (+)-Germacrene A Synthase

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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

inferredcites →https://doi.org/10.1002/anie.201103110openalex-snapshot

Terpene Biosynthesis: Modularity Rules

inferredcites →https://doi.org/10.1002/anie.201301362openalex-snapshot

High‐Throughput Screening for Terpene‐Synthase‐Cyclization Activity and Directed Evolution of a Terpene Synthase

inferredcites →https://doi.org/10.1002/cbic.200700219openalex-snapshot

Aristolochene Synthase‐Catalyzed Cyclization of 2‐Fluorofarnesyl‐Diphosphate to 2‐Fluorogermacrene A

inferredcites →https://doi.org/10.1002/cbic.200700398openalex-snapshot

Interception of the Enzymatic Conversion of Farnesyl Diphosphate to 5‐Epi‐Aristolochene by Using a Fluoro Substrate Analogue: 1‐Fluorogermacrene A from (2E,6Z)‐6‐Fluorofarnesyl Diphosphate

inferredcites →https://doi.org/10.1002/minf.201100087openalex-snapshot

A Mechanism for Evolving Novel Plant Sesquiterpene Synthase Function

inferredcites →https://doi.org/10.1007/bf02167631openalex-snapshot

The isoprene rule and the biogenesis of terpenic compounds

inferredcites →https://doi.org/10.1007/s00425-008-0700-xopenalex-snapshot

Molecular cloning and functional characterization of α-humulene synthase, a possible key enzyme of zerumbone biosynthesis in shampoo ginger (Zingiber zerumbet Smith)

inferredcites →https://doi.org/10.1007/s10529-005-0681-9openalex-snapshot

Point mutation of (+)-germacrene A synthase from Ixeris dentata

inferredcites →https://doi.org/10.1016/0040-4020(59)80055-7openalex-snapshot

Stereochemical implications in sesquiterpene biogenesis

inferredcites →https://doi.org/10.1016/0040-4020(60)80047-6openalex-snapshot

Studies in sesquiterpenes—XVIII

inferredcites →https://doi.org/10.1016/j.abb.2004.06.030openalex-snapshot

Enantiospecific (+)- and (−)-germacrene D synthases, cloned from goldenrod, reveal a functionally active variant of the universal isoprenoid-biosynthesis aspartate-rich motif

inferredcites →https://doi.org/10.1016/j.abb.2005.02.012openalex-snapshot

Expression, purification, and characterization of recombinant amorpha-4,11-diene synthase from Artemisia annua L.

inferredcites →https://doi.org/10.1016/j.abb.2005.09.002openalex-snapshot

Stereochemistry and deuterium isotope effects associated with the cyclization-rearrangements catalyzed by tobacco epiaristolochene and hyoscyamus premnaspirodiene synthases, and the chimeric CH4 hybrid cyclase

inferredcites →https://doi.org/10.1016/j.abb.2006.02.026openalex-snapshot

Isoprenoid biosynthesis in Artemisia annua: Cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library

inferredcites →https://doi.org/10.1016/j.cbpa.2006.08.011openalex-snapshot

Enzyme promiscuity: evolutionary and mechanistic aspects

inferredcites →https://doi.org/10.1016/j.cbpa.2007.12.008openalex-snapshot

Unearthing the roots of the terpenome

inferredcites →https://doi.org/10.1016/j.phytochem.2009.07.030openalex-snapshot

Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants

inferredcites →https://doi.org/10.1016/j.tet.2007.04.037openalex-snapshot

Conformational analysis of (+)-germacrene A by variable-temperature NMR and NOE spectroscopy

inferredcites →https://doi.org/10.1016/s0031-9422(02)00165-6openalex-snapshot

(+)-(10R)-Germacrene A synthase from goldenrod, Solidago canadensis; cDNA isolation, bacterial expression and functional analysis

inferredcites →https://doi.org/10.1016/s0040-4039(00)82056-0openalex-snapshot

Biomimetic germacrene-humulene rearrangement

inferredcites →https://doi.org/10.1016/s0040-4039(01)94894-4openalex-snapshot

Studies on the mechanism of sesquiterpene biosynthesis humulene-germacrene rearrangement

inferredcites →https://doi.org/10.1016/s0959-440x(98)80088-2openalex-snapshot

Managing and manipulating carbocations in biology: terpenoid cyclase structure and mechanism

inferredcites →https://doi.org/10.1016/s0969-2126(00)00065-4openalex-snapshot

Volume changes on protein folding

inferredcites →https://doi.org/10.1021/ar00115a005openalex-snapshot

Isoprenoid biosynthesis. Stereochemistry of the cyclization of allylic pyrophosphates

inferredcites →https://doi.org/10.1021/bi00008a010openalex-snapshot

Trichodiene Synthase. Substrate Specificity and Inhibition

inferredcites →https://doi.org/10.1021/bi00391a025openalex-snapshot

Isotopically sensitive branching in the formation of cyclic monoterpenes: proof that (-)-.alpha.-pinene and (-)-.beta.-pinene are synthesized by the same monoterpene cyclase via deprotonation of a common intermediate

inferredcites →https://doi.org/10.1021/bi050059oopenalex-snapshot

Molecular Recognition of the Substrate Diphosphate Group Governs Product Diversity in Trichodiene Synthase Mutants ,

inferredcites →https://doi.org/10.1021/bi400797copenalex-snapshot

Unexpected Reactivity of 2-Fluorolinalyl Diphosphate in the Active Site of Crystalline 2-Methylisoborneol Synthase

inferredcites →https://doi.org/10.1021/bi900483bopenalex-snapshot

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

inferredcites →https://doi.org/10.1021/bi963018oopenalex-snapshot

Pre-Steady-State Kinetic Analysis of the Trichodiene Synthase Reaction Pathway

inferredcites →https://doi.org/10.1021/bi963019gopenalex-snapshot

Pre-Steady-State Study of Recombinant Sesquiterpene Cyclases

inferredcites →https://doi.org/10.1021/cb900295gopenalex-snapshot

Structural Elucidation of Cisoid and Transoid Cyclization Pathways of a Sesquiterpene Synthase Using 2-Fluorofarnesyl Diphosphates

inferredcites →https://doi.org/10.1021/cr00081a004openalex-snapshot

Biosynthesis and catabolism of monoterpenoids

inferredcites →https://doi.org/10.1021/cr00105a002openalex-snapshot

Enzymic formation of sesquiterpenes

inferredcites →https://doi.org/10.1021/cr050286wopenalex-snapshot

Structural Biology and Chemistry of the Terpenoid Cyclases

inferredcites →https://doi.org/10.1021/ja00282a037openalex-snapshot

Isotopically sensitive branching and its effect on the observed intramolecular isotope effects in cytochrome P-450 catalyzed reactions: a new method for the estimation of intrinsic isotope effects

inferredcites →https://doi.org/10.1021/ja050592ropenalex-snapshot

Taxadiene Synthase-Catalyzed Cyclization of 6-Fluorogeranylgeranyl Diphosphate to 7-Fluoroverticillenes

inferredcites →https://doi.org/10.1021/ja0771282openalex-snapshot

A Common Mechanism for Branching, Cyclopropanation, and Cyclobutanation Reactions in the Isoprenoid Biosynthetic Pathway

inferredcites →https://doi.org/10.1021/ja205927uopenalex-snapshot

Probing Eudesmane Cation−π Interactions in Catalysis by Aristolochene Synthase with Non-canonical Amino Acids

inferredcites →https://doi.org/10.1021/ja211820popenalex-snapshot

A 1,6-Ring Closure Mechanism for (+)-δ-Cadinene Synthase?

inferredcites →https://doi.org/10.1021/ja3043245openalex-snapshot

Effect of Isotopically Sensitive Branching on Product Distribution for Pentalenene Synthase: Support for a Mechanism Predicted by Quantum Chemistry

inferredcites →https://doi.org/10.1021/ja311022sopenalex-snapshot

Probing the Mechanism of 1,4-Conjugate Elimination Reactions Catalyzed by Terpene Synthases

inferredcites →https://doi.org/10.1021/ja909251ropenalex-snapshot

Doubly Deuterium-Labeled Patchouli Alcohol from Cyclization of Singly Labeled [2-2H1]Farnesyl Diphosphate Catalyzed by Recombinant Patchoulol Synthase

inferredcites →https://doi.org/10.1021/ja909886qopenalex-snapshot

Bisabolyl-Derived Sesquiterpenes from Tobacco 5-Epi-aristolochene Synthase-Catalyzed Cyclization of (2Z,6E)-Farnesyl Diphosphate

inferredcites →https://doi.org/10.1021/ja992271jopenalex-snapshot

Theoretical Studies of Carbocations in Ion Pairs. 5.1Structures and Interconversion of the 3-Methyl-2-butyl Cation and 2,3-Dimethyl-1-Protonated Cyclopropane

inferredcites →https://doi.org/10.1021/ja993584hopenalex-snapshot

Demonstration of Germacrene A as an Intermediate in 5-Epi-aristolochene Synthase Catalysis

inferredcites →https://doi.org/10.1021/jo00067a037openalex-snapshot

Regiospecificity and isotope effects associated with the methyl-methylene eliminations in the enzyme-catalyzed biosynthesis of (R)- and (S)-limonene

inferredcites →https://doi.org/10.1021/jo049951bopenalex-snapshot

Isotopic Scrambling in Di-13C-labeled 2-Butyl Cation: Evidence for a Protonated Cyclopropane Intermediate

inferredcites →https://doi.org/10.1038/nature04607openalex-snapshot

Designed divergent evolution of enzyme function

inferredcites →https://doi.org/10.1038/nature09628openalex-snapshot

Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis

inferredcites →https://doi.org/10.1038/nature10625openalex-snapshot

The Medicago genome provides insight into the evolution of rhizobial symbioses

inferredcites →https://doi.org/10.1038/nchembio.113openalex-snapshot

Quantitative exploration of the catalytic landscape separating divergent plant sesquiterpene synthases

inferredcites →https://doi.org/10.1038/ng1482openalex-snapshot

The 'evolvability' of promiscuous protein functions

inferredcites →https://doi.org/10.1038/nrm2805openalex-snapshot

Exploring protein fitness landscapes by directed evolution

inferredcites →https://doi.org/10.1039/b709562gopenalex-snapshot

Probing the reaction mechanism of aristolochene synthase with 12,13-difluorofarnesyl diphosphate

inferredcites →https://doi.org/10.1039/b817194gopenalex-snapshot

6- and 14-Fluoro farnesyl diphosphate: mechanistic probes for the reaction catalysed by aristolochene synthase

inferredcites →https://doi.org/10.1039/b917107jopenalex-snapshot

The carbocation continuum in terpene biosynthesis—where are the secondary cations?

inferredcites →https://doi.org/10.1039/c0cc02960bopenalex-snapshot

Electrostatic effects on (di)terpene synthase product outcome

inferredcites →https://doi.org/10.1039/c1np00060hopenalex-snapshot

Sesquiterpene synthases: Passive catalysts or active players?

inferredcites →https://doi.org/10.1039/c2cc17588fopenalex-snapshot

The role of aristolochene synthase in diphosphate activation

inferredcites →https://doi.org/10.1039/c2cc35542fopenalex-snapshot

Chemoenzymatic preparation of germacrene analogues

inferredcites →https://doi.org/10.1039/c2np20059gopenalex-snapshot

Terpenoid synthase structures: a so far incomplete view of complex catalysis

inferredcites →https://doi.org/10.1039/c39810000354openalex-snapshot

The induced kinetic isotope effect as a tool for mechanistic discrimination

inferredcites →https://doi.org/10.1039/cs9720100163openalex-snapshot

Isotope effect studies of elimination reactions

inferredcites →https://doi.org/10.1039/qr9571100189openalex-snapshot

Recent advances in sesquiterpenoid chemistry

inferredcites →https://doi.org/10.1039/qr9672100331openalex-snapshot

Sesquiterpene biogenesis

inferredcites →https://doi.org/10.1042/bj20121818openalex-snapshot

C-24-methylation of 26-fluorocycloartenols by recombinant sterol C-24-methyltransferase from soybean: evidence for channel switching and its phylogenetic implications

inferredcites →https://doi.org/10.1042/bj20130041openalex-snapshot

Rational engineering of plasticity residues of sesquiterpene synthases from Artemisia annua: product specificity and catalytic efficiency

inferredcites →https://doi.org/10.1073/pnas.0601605103openalex-snapshot

Identifying and manipulating structural determinates linking catalytic specificities in terpene synthases

inferredcites →https://doi.org/10.1073/pnas.0611454104openalex-snapshot

Following evolution's lead to a single residue switch for diterpene synthase product outcome

inferredcites →https://doi.org/10.1073/pnas.232591099openalex-snapshot

Bornyl diphosphate synthase: Structure and strategy for carbocation manipulation by a terpenoid cyclase

inferredcites →https://doi.org/10.1073/pnas.95.8.4126openalex-snapshot

Plant terpenoid synthases: Molecular biology and phylogenetic analysis

inferredcites →https://doi.org/10.1074/jbc.273.4.2078openalex-snapshot

Sesquiterpene Synthases from Grand Fir (Abies grandis)

inferredcites →https://doi.org/10.1093/genetics/158.2.811openalex-snapshot

Genomic Organization of Plant Terpene Synthases and Molecular Evolutionary Implications

inferredcites →https://doi.org/10.1104/pp.111.179648openalex-snapshot

The Tomato Terpene Synthase Gene Family

inferredcites →https://doi.org/10.1104/pp.117.4.1381openalex-snapshot

(+)-Germacrene A Biosynthesis

inferredcites →https://doi.org/10.1105/tpc.106.047779openalex-snapshot

Rational Conversion of Substrate and Product Specificity in a Salvia Monoterpene Synthase: Structural Insights into the Evolution of Terpene Synthase Function

inferredcites →https://doi.org/10.1105/tpc.107.057885openalex-snapshot

A Novel Pathway for Sesquiterpene Biosynthesis fromZ,Z-Farnesyl Pyrophosphate in the Wild TomatoSolanum habrochaites

inferredcites →https://doi.org/10.1126/science.1137786openalex-snapshot

Chimeras of Two Isoprenoid Synthases Catalyze All Four Coupling Reactions in Isoprenoid Biosynthesis

inferredcites →https://doi.org/10.1126/science.1217411openalex-snapshot

The Rise of Chemodiversity in Plants

inferredcites →https://doi.org/10.1126/science.277.5333.1815openalex-snapshot

Structural Basis for Cyclic Terpene Biosynthesis by Tobacco 5-Epi-Aristolochene Synthase

inferredcites →https://doi.org/10.1351/pac-con-09-09-37openalex-snapshot

Trinuclear metal clusters in catalysis by terpenoid synthases

What points at this work

Incoming claims: where this work appears in other papers’ reference lists and arguments.

inferred← citeshttps://doi.org/10.1016/j.phytochem.2020.112286zenodo-depositor-declared

Site-directed mutagenesis of β sesquiphellandrene synthase enhances enzyme promiscuity

inferred← citeshttps://doi.org/10.1016/j.phytochem.2021.112818zenodo-depositor-declared

Humulane-type and germacrane-type sesquiterpenoids from the fruits of Xanthium spinosum Linn.

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Effiziente chemoenzymatische Synthese von Dihydroartemisinaldehyd

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Bedeutung der inhärenten Substratreaktivität bei enzymvermittelten Cyclisierungen/Umlagerungen von Carbokationen

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Erweiterung des synthetischen Potenzials von Sesquiterpencyclasen zur Erzeugung von nichtnatürlichen Terpenoiden

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Characterization and Engineering of Two Highly Paralogous Sesquiterpene Synthases Reveal a Regioselective Reprotonation Switch

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An Efficient Chemoenzymatic Synthesis of Dihydroartemisinic Aldehyde

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Importance of Inherent Substrate Reactivity in Enzyme‐Promoted Carbocation Cyclization/Rearrangements

inferred← citeshttps://doi.org/10.1002/anie.201805526openalex-snapshot

Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids

inferred← citeshttps://doi.org/10.1002/anie.202315674openalex-snapshot

Characterization and Engineering of Two Highly Paralogous Sesquiterpene Synthases Reveal a Regioselective Reprotonation Switch

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Engineering Escherichia coli BL21 (DE3) for high‐yield production of germacrene A, a precursor of β‐elemene via combinatorial metabolic engineering strategies

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Moonlighting Metals: Insights into Regulation of Cyclization Pathways in Fungal Δ6‐Protoilludene Sesquiterpene Synthases

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Nucleophilic Water Capture or Proton Loss: Single Amino Acid Switch Converts δ‐Cadinene Synthase into Germacradien‐4‐ol Synthase

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Sesquiterpene Synthase‐Catalysed Formation of a New Medium‐Sized Cyclic Terpenoid Ether from Farnesyl Diphosphate Analogues

inferred← citeshttps://doi.org/10.1002/cbic.70265openalex-snapshot

Designed Water Capture in Terpene Synthase Catalysis

inferred← citeshttps://doi.org/10.1007/s00425-018-2986-7openalex-snapshot

In planta and in silico characterization of five sesquiterpene synthases from Vitis vinifera (cv. Shiraz) berries

inferred← citeshttps://doi.org/10.1007/s11101-022-09833-0openalex-snapshot

Recent advances in biosynthesis and pharmacology of β-elemene

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Production of non-natural terpenoids through chemoenzymatic synthesis using substrate analogs

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Concise synthesis of artemisinin from a farnesyl diphosphate analogue

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Cloning and functional characterization of three sesquiterpene synthase genes from Chamaecyparis formosensis Matsumura

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The T296V Mutant of Amorpha-4,11-diene Synthase Is Defective in Allylic Diphosphate Isomerization but Retains the Ability To Cyclize the Intermediate (3R)-Nerolidyl Diphosphate to Amorpha-4,11-diene

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Sesquiterpene Synthases of Zanthoxylum ailanthoides: Sources of Unique Aromas of a Folklore Plant in Taiwan

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Immunomodulatory Constituents of Conocephalum conicum (Snake Liverwort) and the Relationship of Isolepidozenes to Germacranes and Humulanes

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Sesquiterpenoids Isolated from Two Species of the Asteriscus Alliance

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Methyl-Shifted Farnesyldiphosphate Derivatives Are Substrates for Sesquiterpene Cyclases

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Computer-Informed Engineering: A New Class I Sesquiterpene Synthase JeSTS4 for the Synthesis of an Unusual C10-(S)-Bicyclogermacrene

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Simulation-Guided Engineering Enables a Functional Switch in Selinadiene Synthase toward Hydroxylation

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Resolution of the ABA Biosynthesis Controversy: Discovery of a Dihydroxylating Terpene Synthase and Its Convergent Evolution

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The amino-terminal segment in the β-domain of δ-cadinene synthase is essential for catalysis

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Silent catalytic promiscuity in the high-fidelity terpene cyclase δ-cadinene synthase

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1,10/1,11-Cyclization catalyzed by diverged plant sesquiterpene synthases is dependent on a single residue

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