Probing the mechanism of 1,4-conjugate elimination reactions catalyzed by terpene synthases.
Identifieur interne : 002936 ( Main/Exploration ); précédent : 002935; suivant : 002937Probing the mechanism of 1,4-conjugate elimination reactions catalyzed by terpene synthases.
Auteurs : Juan A. Faraldos [Royaume-Uni] ; Veronica Gonzalez ; Amang Li ; Fanglei Yu ; Mustafa Köksal ; David W. Christianson ; Rudolf K. AllemannSource :
- Journal of the American Chemical Society [ 1520-5126 ] ; 2012.
Descripteurs français
- KwdFr :
- Alkyl et aryl transferases (métabolisme), Butadiènes (métabolisme), Composés organiques du phosphore (métabolisme), Hémiterpènes (métabolisme), Mentha (métabolisme), Pentanes (métabolisme), Polyisoprényl-phosphates (métabolisme), Populus (métabolisme), Protéines recombinantes (métabolisme), Protéines végétales (métabolisme), Pyrophosphatases (métabolisme), Sesquiterpènes (métabolisme).
- MESH :
English descriptors
- KwdEn :
- Alkyl and Aryl Transferases (metabolism), Butadienes (metabolism), Hemiterpenes (metabolism), Mentha (metabolism), Organophosphorus Compounds (metabolism), Pentanes (metabolism), Plant Proteins (metabolism), Polyisoprenyl Phosphates (metabolism), Populus (metabolism), Pyrophosphatases (metabolism), Recombinant Proteins (metabolism), Sesquiterpenes (metabolism).
- MESH :
- chemical , metabolism : Alkyl and Aryl Transferases, Butadienes, Hemiterpenes, Organophosphorus Compounds, Pentanes, Plant Proteins, Polyisoprenyl Phosphates, Pyrophosphatases, Recombinant Proteins, Sesquiterpenes.
- metabolism : Mentha, Populus.
Abstract
The reaction mechanisms of (E)-β-farnesene synthase (EBFS) and isoprene synthase (ISPS), enzymes that catalyze a formal regiospecific 1,4-conjugate elimination of hydrogen diphosphate from (E,E)-farnesyl and dimethylallyl diphosphate (FDP and DMADP) to generate the semiochemicals (E)-β-farnesene and isoprene, respectively, were probed with substrate analogs and kinetic measurements. The results support stepwise reaction mechanisms through analogous enzyme-bound allylic cationic intermediates. For EBFS, we demonstrate that the elimination reaction can proceed via the enzyme-bound intermediate trans-nerolidyl diphosphate, while for ISPS the intermediacy of 2-methylbut-3-enyl 2-diphosphate can be inferred from the product outcome when deuterated DMADPs are used as substrates. Possible implications derived from the mechanistic details of the EBFS-catalyzed reaction for the evolution of sesquiterpene synthases are discussed.
DOI: 10.1021/ja311022s
PubMed: 23214943
PubMed Central: PMC3530649
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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Christianson</name></author><author><name sortKey="Allemann, Rudolf K" sort="Allemann, Rudolf K" uniqKey="Allemann R" first="Rudolf K" last="Allemann">Rudolf K. Allemann</name></author></analytic><series><title level="j">Journal of the American Chemical Society</title><idno type="eISSN">1520-5126</idno><imprint><date when="2012" type="published">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alkyl and Aryl Transferases (metabolism)</term><term>Butadienes (metabolism)</term><term>Hemiterpenes (metabolism)</term><term>Mentha (metabolism)</term><term>Organophosphorus Compounds (metabolism)</term><term>Pentanes (metabolism)</term><term>Plant Proteins (metabolism)</term><term>Polyisoprenyl Phosphates (metabolism)</term><term>Populus (metabolism)</term><term>Pyrophosphatases (metabolism)</term><term>Recombinant Proteins (metabolism)</term><term>Sesquiterpenes (metabolism)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Alkyl et aryl transferases (métabolisme)</term><term>Butadiènes (métabolisme)</term><term>Composés organiques du phosphore (métabolisme)</term><term>Hémiterpènes (métabolisme)</term><term>Mentha (métabolisme)</term><term>Pentanes (métabolisme)</term><term>Polyisoprényl-phosphates (métabolisme)</term><term>Populus (métabolisme)</term><term>Protéines recombinantes (métabolisme)</term><term>Protéines végétales (métabolisme)</term><term>Pyrophosphatases (métabolisme)</term><term>Sesquiterpènes (métabolisme)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Alkyl and Aryl Transferases</term><term>Butadienes</term><term>Hemiterpenes</term><term>Organophosphorus Compounds</term><term>Pentanes</term><term>Plant Proteins</term><term>Polyisoprenyl Phosphates</term><term>Pyrophosphatases</term><term>Recombinant Proteins</term><term>Sesquiterpenes</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Mentha</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Alkyl et aryl transferases</term><term>Butadiènes</term><term>Composés organiques du phosphore</term><term>Hémiterpènes</term><term>Mentha</term><term>Pentanes</term><term>Polyisoprényl-phosphates</term><term>Populus</term><term>Protéines recombinantes</term><term>Protéines végétales</term><term>Pyrophosphatases</term><term>Sesquiterpènes</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The reaction mechanisms of (E)-β-farnesene synthase (EBFS) and isoprene synthase (ISPS), enzymes that catalyze a formal regiospecific 1,4-conjugate elimination of hydrogen diphosphate from (E,E)-farnesyl and dimethylallyl diphosphate (FDP and DMADP) to generate the semiochemicals (E)-β-farnesene and isoprene, respectively, were probed with substrate analogs and kinetic measurements. The results support stepwise reaction mechanisms through analogous enzyme-bound allylic cationic intermediates. For EBFS, we demonstrate that the elimination reaction can proceed via the enzyme-bound intermediate trans-nerolidyl diphosphate, while for ISPS the intermediacy of 2-methylbut-3-enyl 2-diphosphate can be inferred from the product outcome when deuterated DMADPs are used as substrates. Possible implications derived from the mechanistic details of the EBFS-catalyzed reaction for the evolution of sesquiterpene synthases are discussed.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">23214943</PMID><DateCompleted><Year>2013</Year><Month>05</Month><Day>30</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>13</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5126</ISSN><JournalIssue CitedMedium="Internet"><Volume>134</Volume><Issue>51</Issue><PubDate><Year>2012</Year><Month>Dec</Month><Day>26</Day></PubDate></JournalIssue><Title>Journal of the American Chemical Society</Title><ISOAbbreviation>J Am Chem Soc</ISOAbbreviation></Journal><ArticleTitle>Probing the mechanism of 1,4-conjugate elimination reactions catalyzed by terpene synthases.</ArticleTitle><Pagination><MedlinePgn>20844-8</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/ja311022s</ELocationID><Abstract><AbstractText>The reaction mechanisms of (E)-β-farnesene synthase (EBFS) and isoprene synthase (ISPS), enzymes that catalyze a formal regiospecific 1,4-conjugate elimination of hydrogen diphosphate from (E,E)-farnesyl and dimethylallyl diphosphate (FDP and DMADP) to generate the semiochemicals (E)-β-farnesene and isoprene, respectively, were probed with substrate analogs and kinetic measurements. The results support stepwise reaction mechanisms through analogous enzyme-bound allylic cationic intermediates. For EBFS, we demonstrate that the elimination reaction can proceed via the enzyme-bound intermediate trans-nerolidyl diphosphate, while for ISPS the intermediacy of 2-methylbut-3-enyl 2-diphosphate can be inferred from the product outcome when deuterated DMADPs are used as substrates. Possible implications derived from the mechanistic details of the EBFS-catalyzed reaction for the evolution of sesquiterpene synthases are discussed.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Faraldos</LastName><ForeName>Juan A</ForeName><Initials>JA</Initials><AffiliationInfo><Affiliation>School of Chemistry and Cardiff Catalysis Institute, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, United Kingdom.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gonzalez</LastName><ForeName>Veronica</ForeName><Initials>V</Initials></Author><Author ValidYN="Y"><LastName>Li</LastName><ForeName>Amang</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Yu</LastName><ForeName>Fanglei</ForeName><Initials>F</Initials></Author><Author ValidYN="Y"><LastName>Köksal</LastName><ForeName>Mustafa</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Christianson</LastName><ForeName>David W</ForeName><Initials>DW</Initials></Author><Author ValidYN="Y"><LastName>Allemann</LastName><ForeName>Rudolf K</ForeName><Initials>RK</Initials></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>R01 GM056838</GrantID><Acronym>GM</Acronym><Agency>NIGMS NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>BB/G003572/1</GrantID><Agency>Biotechnology and Biological Sciences Research Council</Agency><Country>United Kingdom</Country></Grant><Grant><GrantID>GM56838</GrantID><Acronym>GM</Acronym><Agency>NIGMS NIH HHS</Agency><Country>United States</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D052061">Research Support, N.I.H., Extramural</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2012</Year><Month>12</Month><Day>11</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Am Chem Soc</MedlineTA><NlmUniqueID>7503056</NlmUniqueID><ISSNLinking>0002-7863</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D002070">Butadienes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D045782">Hemiterpenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009943">Organophosphorus Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010420">Pentanes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010940">Plant Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011106">Polyisoprenyl Phosphates</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011994">Recombinant Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D012717">Sesquiterpenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0A62964IBU</RegistryNumber><NameOfSubstance UI="C005059">isoprene</NameOfSubstance></Chemical><Chemical><RegistryNumber>18794-84-8</RegistryNumber><NameOfSubstance UI="C062671">beta-farnesene</NameOfSubstance></Chemical><Chemical><RegistryNumber>358-72-5</RegistryNumber><NameOfSubstance UI="C043060">3,3-dimethylallyl pyrophosphate</NameOfSubstance></Chemical><Chemical><RegistryNumber>79W6B01D07</RegistryNumber><NameOfSubstance UI="C004808">farnesyl pyrophosphate</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.5.-</RegistryNumber><NameOfSubstance UI="D019883">Alkyl and Aryl Transferases</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.5.1.-</RegistryNumber><NameOfSubstance UI="C093854">isoprene synthase</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.5.1.-</RegistryNumber><NameOfSubstance UI="C108877">terpene synthase</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.6.1.-</RegistryNumber><NameOfSubstance UI="D011755">Pyrophosphatases</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.6.1.-</RegistryNumber><NameOfSubstance UI="C109459">beta-farnesene synthase</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D019883" MajorTopicYN="N">Alkyl and Aryl Transferases</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002070" MajorTopicYN="N">Butadienes</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045782" MajorTopicYN="N">Hemiterpenes</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D027541" MajorTopicYN="N">Mentha</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009943" MajorTopicYN="N">Organophosphorus Compounds</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010420" MajorTopicYN="N">Pentanes</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010940" MajorTopicYN="N">Plant Proteins</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011106" MajorTopicYN="N">Polyisoprenyl Phosphates</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D032107" MajorTopicYN="N">Populus</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011755" MajorTopicYN="N">Pyrophosphatases</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011994" MajorTopicYN="N">Recombinant Proteins</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012717" MajorTopicYN="N">Sesquiterpenes</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2012</Year><Month>12</Month><Day>11</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate 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Allemann</name><name sortKey="Christianson, David W" sort="Christianson, David W" uniqKey="Christianson D" first="David W" last="Christianson">David W. Christianson</name><name sortKey="Gonzalez, Veronica" sort="Gonzalez, Veronica" uniqKey="Gonzalez V" first="Veronica" last="Gonzalez">Veronica Gonzalez</name><name sortKey="Koksal, Mustafa" sort="Koksal, Mustafa" uniqKey="Koksal M" first="Mustafa" last="Köksal">Mustafa Köksal</name><name sortKey="Li, Amang" sort="Li, Amang" uniqKey="Li A" first="Amang" last="Li">Amang Li</name><name sortKey="Yu, Fanglei" sort="Yu, Fanglei" uniqKey="Yu F" first="Fanglei" last="Yu">Fanglei Yu</name></noCountry><country name="Royaume-Uni"><noRegion><name sortKey="Faraldos, Juan A" sort="Faraldos, Juan A" uniqKey="Faraldos J" first="Juan A" last="Faraldos">Juan A. Faraldos</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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