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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>
</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>
<pmc article-type="research-article"><pmc-comment>The publisher of this article does not allow downloading of the full text in XML form.</pmc-comment>
<front><journal-meta><journal-id journal-id-type="nlm-ta">J Biol Chem</journal-id>
<journal-id journal-id-type="publisher-id">jbc</journal-id>
<journal-title-group><journal-title>The Journal of Biological Chemistry</journal-title>
</journal-title-group>
<issn pub-type="ppub">0021-9258</issn>
<issn pub-type="epub">1083-351X</issn>
<publisher><publisher-name>American Society for Biochemistry and Molecular Biology</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">18524777</article-id>
<article-id pub-id-type="pmc">3258946</article-id>
<article-id pub-id-type="publisher-id">20779</article-id>
<article-id pub-id-type="doi">10.1074/jbc.M802682200</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Enzyme Catalysis and Regulation</subject>
</subj-group>
</article-categories>
<title-group><article-title>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>
</article-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Köllner</surname>
<given-names>Tobias G.</given-names>
</name>
</contrib>
<contrib contrib-type="author"><name><surname>Schnee</surname>
<given-names>Christiane</given-names>
</name>
</contrib>
<contrib contrib-type="author"><name><surname>Li</surname>
<given-names>Shenghong</given-names>
</name>
</contrib>
<contrib contrib-type="author"><name><surname>Svatoš</surname>
<given-names>Aleš</given-names>
</name>
</contrib>
<contrib contrib-type="author"><name><surname>Schneider</surname>
<given-names>Bernd</given-names>
</name>
</contrib>
<contrib contrib-type="author"><name><surname>Gershenzon</surname>
<given-names>Jonathan</given-names>
</name>
</contrib>
<contrib contrib-type="author"><name><surname>Degenhardt</surname>
<given-names>Jörg</given-names>
</name>
<xref ref-type="corresp" rid="cor1">1</xref>
</contrib>
</contrib-group>
<aff id="d31e67">Max Planck Institute for Chemical Ecology, Hans-Knöll Strasse 8, D-07745 Jena, Germany</aff>
<author-notes><corresp id="cor1"><label>1</label>
To whom correspondence should be addressed. Fax: 49-3641-571302; E-mail:
<email>degenhardt@ice.mpg.de</email>
.
</corresp>
</author-notes>
<pub-date pub-type="ppub"><day>25</day>
<month>7</month>
<year>2008</year>
</pub-date>
<volume>283</volume>
<issue>30</issue>
<fpage>20779</fpage>
<lpage>20788</lpage>
<history><date date-type="received"><day>7</day>
<month>4</month>
<year>2008</year>
</date>
<date date-type="rev-recd"><day>21</day>
<month>5</month>
<year>2008</year>
</date>
</history>
<permissions><copyright-statement>Copyright © 2008, The American Society for Biochemistry and
Molecular Biology, Inc.</copyright-statement>
<copyright-year>2008</copyright-year>
</permissions>
<self-uri xlink:title="pdf" xlink:href="zbc03008020779.pdf"></self-uri>
<abstract><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>
</abstract>
</article-meta>
<notes><fn-group><fn id="fn1"><label>*</label>
<p>The work was supported by <funding-source>German Research
Foundation</funding-source>
Grant <award-id>DE8372-2</award-id>
(to J. D. and
J. G.) and funds from the <funding-source>Max Planck Society</funding-source>
.
The costs of publication of this article were defrayed in part by the payment
of page charges. This article must therefore be hereby marked
“<italic>advertisement</italic>
”in accordance with 18 U.S.C. Section 1734
solely to indicate this fact.</p>
<p><italic>The nucleotide sequence(s) reported in this paper has been submitted to
the GenBank</italic>
™<italic>/EBI Data Bank with accession number(s) AY518315
and EU716166.</italic>
</p>
</fn>
</fn-group>
</notes>
</front>
</pmc>
</record>
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