Protonation of a Neutral (S)-β-Bisabolene Intermediate Is Involved in (S)-β-Macrocarpene Formation by the Maize Sesquiterpene Synthases TPS6 and TPS11*
Identifieur interne : 000842 ( Ncbi/Curation ); précédent : 000841; suivant : 000843Protonation of a Neutral (S)-β-Bisabolene Intermediate Is Involved in (S)-β-Macrocarpene Formation by the Maize Sesquiterpene Synthases TPS6 and TPS11*
Auteurs : Tobias G. Köllner ; Christiane Schnee ; Shenghong Li ; Aleš Svatoš ; Bernd Schneider ; Jonathan Gershenzon ; Jörg DegenhardtSource :
- The Journal of Biological Chemistry [ 0021-9258 ] ; 2008.
Abstract
Terpene synthases are responsible for the large diversity of terpene carbon skeletons found in plants. The unique, carbocationic reaction mechanism of these enzymes can form multiple products from a single prenyl diphosphate substrate. Two maize genes were isolated that encode very similar sesquiterpene synthases, TPS6 and TPS11, which both produce β-bisabolene, a common monocyclic sesquiterpene, and β-macrocarpene, an uncommon bicyclic olefin. Investigation of the reaction mechanism showed that the formation of β-macrocarpene proceeds via a neutral β-bisabolene intermediate and requires reprotonation by a proton that may ultimately be abstracted from water. This reprotonation is dependent on the pH and the presence of a Mg2+ cofactor. Mutational analysis of the enzyme demonstrated that a highly conserved tyrosine residue in the active center of the enzymes is important for the protonation process. TPS6 and TPS11 are transcribed both in leaves and roots of maize, but the respective terpene products were only detected in roots. The expression in roots was up-regulated by herbivore damage to the leaves, suggesting a long distance signal transduction cascade between leaves and roots.
Url:
DOI: 10.1074/jbc.M802682200
PubMed: 18524777
PubMed Central: 3258946
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Protonation of a Neutral (<italic>S</italic>)-β-Bisabolene Intermediate Is
Involved in (<italic>S</italic>)-β-Macrocarpene Formation by the Maize
Sesquiterpene Synthases TPS6 and
TPS11<xref ref-type="fn" rid="fn1">*</xref></title><author><name sortKey="Kollner, Tobias G" sort="Kollner, Tobias G" uniqKey="Kollner T" first="Tobias G." last="Köllner">Tobias G. Köllner</name></author><author><name sortKey="Schnee, Christiane" sort="Schnee, Christiane" uniqKey="Schnee C" first="Christiane" last="Schnee">Christiane Schnee</name></author><author><name sortKey="Li, Shenghong" sort="Li, Shenghong" uniqKey="Li S" first="Shenghong" last="Li">Shenghong Li</name></author><author><name sortKey="Svatos, Ales" sort="Svatos, Ales" uniqKey="Svatos A" first="Aleš" last="Svatoš">Aleš Svatoš</name></author><author><name sortKey="Schneider, Bernd" sort="Schneider, Bernd" uniqKey="Schneider B" first="Bernd" last="Schneider">Bernd Schneider</name></author><author><name sortKey="Gershenzon, Jonathan" sort="Gershenzon, Jonathan" uniqKey="Gershenzon J" first="Jonathan" last="Gershenzon">Jonathan Gershenzon</name></author><author><name sortKey="Degenhardt, Jorg" sort="Degenhardt, Jorg" uniqKey="Degenhardt J" first="Jörg" last="Degenhardt">Jörg Degenhardt</name></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">18524777</idno><idno type="pmc">3258946</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3258946</idno><idno type="RBID">PMC:3258946</idno><idno type="doi">10.1074/jbc.M802682200</idno><date when="2008">2008</date><idno type="wicri:Area/Pmc/Corpus">000C65</idno><idno type="wicri:Area/Pmc/Curation">000C64</idno><idno type="wicri:Area/Pmc/Checkpoint">001063</idno><idno type="wicri:Area/Ncbi/Merge">000842</idno><idno type="wicri:Area/Ncbi/Curation">000842</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Protonation of a Neutral (<italic>S</italic>)-β-Bisabolene Intermediate Is
Involved in (<italic>S</italic>)-β-Macrocarpene Formation by the Maize
Sesquiterpene Synthases TPS6 and
TPS11<xref ref-type="fn" rid="fn1">*</xref></title><author><name sortKey="Kollner, Tobias G" sort="Kollner, Tobias G" uniqKey="Kollner T" first="Tobias G." last="Köllner">Tobias G. Köllner</name></author><author><name sortKey="Schnee, Christiane" sort="Schnee, Christiane" uniqKey="Schnee C" first="Christiane" last="Schnee">Christiane Schnee</name></author><author><name sortKey="Li, Shenghong" sort="Li, Shenghong" uniqKey="Li S" first="Shenghong" last="Li">Shenghong Li</name></author><author><name sortKey="Svatos, Ales" sort="Svatos, Ales" uniqKey="Svatos A" first="Aleš" last="Svatoš">Aleš Svatoš</name></author><author><name sortKey="Schneider, Bernd" sort="Schneider, Bernd" uniqKey="Schneider B" first="Bernd" last="Schneider">Bernd Schneider</name></author><author><name sortKey="Gershenzon, Jonathan" sort="Gershenzon, Jonathan" uniqKey="Gershenzon J" first="Jonathan" last="Gershenzon">Jonathan Gershenzon</name></author><author><name sortKey="Degenhardt, Jorg" sort="Degenhardt, Jorg" uniqKey="Degenhardt J" first="Jörg" last="Degenhardt">Jörg Degenhardt</name></author></analytic><series><title level="j">The Journal of Biological Chemistry</title><idno type="ISSN">0021-9258</idno><idno type="eISSN">1083-351X</idno><imprint><date when="2008">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Terpene synthases are responsible for the large diversity of terpene carbon
skeletons found in plants. The unique, carbocationic reaction mechanism of
these enzymes can form multiple products from a single prenyl diphosphate
substrate. Two maize genes were isolated that encode very similar
sesquiterpene synthases, TPS6 and TPS11, which both produce β-bisabolene,
a common monocyclic sesquiterpene, and β-macrocarpene, an uncommon
bicyclic olefin. Investigation of the reaction mechanism showed that the
formation of β-macrocarpene proceeds via a neutral β-bisabolene
intermediate and requires reprotonation by a proton that may ultimately be
abstracted from water. This reprotonation is dependent on the pH and the
presence of a Mg<sup>2+</sup> cofactor. Mutational analysis of the enzyme
demonstrated that a highly conserved tyrosine residue in the active center of
the enzymes is important for the protonation process. TPS6 and TPS11 are
transcribed both in leaves and roots of maize, but the respective terpene
products were only detected in roots. The expression in roots was up-regulated
by herbivore damage to the leaves, suggesting a long distance signal
transduction cascade between leaves and roots.</p></div></front></TEI></record>Pour manipuler ce document sous Unix (Dilib)
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Sesquiterpene Synthases TPS6 and
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