Functional characterization of two acyltransferases from Populus trichocarpa capable of synthesizing benzyl benzoate and salicyl benzoate, potential intermediates in salicinoid phenolic glycoside biosynthesis.
Identifieur interne : 001D55 ( Main/Exploration ); précédent : 001D54; suivant : 001D56Functional characterization of two acyltransferases from Populus trichocarpa capable of synthesizing benzyl benzoate and salicyl benzoate, potential intermediates in salicinoid phenolic glycoside biosynthesis.
Auteurs : Russell J. Chedgy [Canada] ; Tobias G. Köllner [Allemagne] ; C Peter Constabel [Canada]Source :
- Phytochemistry [ 1873-3700 ] ; 2015.
Descripteurs français
- KwdFr :
- ADN complémentaire (génétique), Acyl coenzyme A (composition chimique), Acyl coenzyme A (métabolisme), Acyltransferases (génétique), Acyltransferases (métabolisme), Alcools benzyliques (métabolisme), Benzoates (composition chimique), Benzoates (métabolisme), Escherichia coli (génétique), Feuilles de plante (métabolisme), Glucosides (métabolisme), Hétérosides (métabolisme), Phénols (métabolisme), Populus (enzymologie), Populus (génétique), Populus (métabolisme), Structure moléculaire (MeSH).
- MESH :
- composition chimique : Acyl coenzyme A, Benzoates.
- enzymologie : Populus.
- génétique : ADN complémentaire, Acyltransferases, Escherichia coli, Populus.
- métabolisme : Acyl coenzyme A, Acyltransferases, Alcools benzyliques, Benzoates, Feuilles de plante, Glucosides, Hétérosides, Phénols, Populus.
- Structure moléculaire.
English descriptors
- KwdEn :
- Acyl Coenzyme A (chemistry), Acyl Coenzyme A (metabolism), Acyltransferases (genetics), Acyltransferases (metabolism), Benzoates (chemistry), Benzoates (metabolism), Benzyl Alcohols (metabolism), DNA, Complementary (genetics), Escherichia coli (genetics), Glucosides (metabolism), Glycosides (metabolism), Molecular Structure (MeSH), Phenols (metabolism), Plant Leaves (metabolism), Populus (enzymology), Populus (genetics), Populus (metabolism).
- MESH :
- chemical , chemistry : Acyl Coenzyme A, Benzoates.
- chemical , genetics : Acyltransferases, DNA, Complementary.
- chemical , metabolism : Acyl Coenzyme A, Acyltransferases, Benzoates, Benzyl Alcohols, Glucosides, Glycosides, Phenols.
- enzymology : Populus.
- genetics : Escherichia coli, Populus.
- metabolism : Plant Leaves, Populus.
- Molecular Structure.
Abstract
Salicinoids are phenolic glycosides (PGs) characteristic of the Salicaceae and are known defenses against insect herbivory. Common examples are salicin, salicortin, tremuloidin, and tremulacin, which accumulate to high concentrations in the leaves and bark of willows and poplars. Although their biosynthetic pathway is not known, recent work has suggested that benzyl benzoate may be a potential biosynthetic intermediate. Two candidate genes, named PtACT47 and PtACT49, encoding BAHD-type acyl transferases were identified and are predicted to produce such benzylated secondary metabolites. Herein described are the cDNA cloning, heterologous expression and in vitro functional characterization of these two BAHD acyltransferases. Recombinant PtACT47 exhibited low substrate selectivity and could utilize acetyl-CoA, benzoyl-CoA, and cinnamoyl-CoA as acyl donors with a variety of alcohols as acyl acceptors. This enzyme showed the greatest Km/Kcat ratio (45.8 nM(-1) s(-1)) and lowest Km values (45.1 μM) with benzoyl-CoA and salicyl alcohol, and was named benzoyl-CoA: salicyl alcohol O-benzoyltransferase (PtSABT). Recombinant PtACT49 utilized a narrower range of substrates, including benzoyl-CoA and acetyl-CoA and a limited number of alcohols. Its highest Km/Kcat (31.8 nM(-1) s(-1)) and lowest Km (55.3 μM) were observed for benzoyl-CoA and benzyl alcohol, and it was named benzoyl-CoA: benzyl alcohol O-benzoyltransferase (PtBEBT). Both enzymes were also capable of synthesizing plant volatile alcohol esters, such as hexenyl benzoate, at trace levels. Although the activities demonstrated are consistent with roles in salicinoid biosynthesis, direct tests of this hypothesis using transgenic poplar must still be performed.
DOI: 10.1016/j.phytochem.2014.10.018
PubMed: 25561400
Affiliations:
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Chedgy</name><affiliation wicri:level="1"><nlm:affiliation>Centre for Forest Biology, Department of Biology, University of Victoria, P.O. Box 3020, STN CSC, Victoria, BC V8W 3N5, Canada.</nlm:affiliation><country xml:lang="fr">Canada</country><wicri:regionArea>Centre for Forest Biology, Department of Biology, University of Victoria, P.O. Box 3020, STN CSC, Victoria, BC V8W 3N5</wicri:regionArea><wicri:noRegion>BC V8W 3N5</wicri:noRegion></affiliation></author><author><name sortKey="Kollner, Tobias G" sort="Kollner, Tobias G" uniqKey="Kollner T" first="Tobias G" last="Köllner">Tobias G. Köllner</name><affiliation wicri:level="1"><nlm:affiliation>Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, 07745 Jena, Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, 07745 Jena</wicri:regionArea><wicri:noRegion>07745 Jena</wicri:noRegion><wicri:noRegion>07745 Jena</wicri:noRegion><wicri:noRegion>07745 Jena</wicri:noRegion></affiliation></author><author><name sortKey="Constabel, C Peter" sort="Constabel, C Peter" uniqKey="Constabel C" first="C Peter" last="Constabel">C Peter Constabel</name><affiliation wicri:level="1"><nlm:affiliation>Centre for Forest Biology, Department of Biology, University of Victoria, P.O. Box 3020, STN CSC, Victoria, BC V8W 3N5, Canada. Electronic address: cpc@uvic.ca.</nlm:affiliation><country xml:lang="fr">Canada</country><wicri:regionArea>Centre for Forest Biology, Department of Biology, University of Victoria, P.O. Box 3020, STN CSC, Victoria, BC V8W 3N5</wicri:regionArea><wicri:noRegion>BC V8W 3N5</wicri:noRegion></affiliation></author></analytic><series><title level="j">Phytochemistry</title><idno type="eISSN">1873-3700</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acyl Coenzyme A (chemistry)</term><term>Acyl Coenzyme A (metabolism)</term><term>Acyltransferases (genetics)</term><term>Acyltransferases (metabolism)</term><term>Benzoates (chemistry)</term><term>Benzoates (metabolism)</term><term>Benzyl Alcohols (metabolism)</term><term>DNA, Complementary (genetics)</term><term>Escherichia coli (genetics)</term><term>Glucosides (metabolism)</term><term>Glycosides (metabolism)</term><term>Molecular Structure (MeSH)</term><term>Phenols (metabolism)</term><term>Plant Leaves (metabolism)</term><term>Populus (enzymology)</term><term>Populus (genetics)</term><term>Populus (metabolism)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN complémentaire (génétique)</term><term>Acyl coenzyme A (composition chimique)</term><term>Acyl coenzyme A (métabolisme)</term><term>Acyltransferases (génétique)</term><term>Acyltransferases (métabolisme)</term><term>Alcools benzyliques (métabolisme)</term><term>Benzoates (composition chimique)</term><term>Benzoates (métabolisme)</term><term>Escherichia coli (génétique)</term><term>Feuilles de plante (métabolisme)</term><term>Glucosides (métabolisme)</term><term>Hétérosides (métabolisme)</term><term>Phénols (métabolisme)</term><term>Populus (enzymologie)</term><term>Populus (génétique)</term><term>Populus (métabolisme)</term><term>Structure moléculaire (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Acyl Coenzyme A</term><term>Benzoates</term></keywords><keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>Acyltransferases</term><term>DNA, Complementary</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Acyl Coenzyme A</term><term>Acyltransferases</term><term>Benzoates</term><term>Benzyl Alcohols</term><term>Glucosides</term><term>Glycosides</term><term>Phenols</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Acyl coenzyme A</term><term>Benzoates</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Populus</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Populus</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Escherichia coli</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>ADN complémentaire</term><term>Acyltransferases</term><term>Escherichia coli</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Plant Leaves</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Acyl coenzyme A</term><term>Acyltransferases</term><term>Alcools benzyliques</term><term>Benzoates</term><term>Feuilles de plante</term><term>Glucosides</term><term>Hétérosides</term><term>Phénols</term><term>Populus</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Molecular Structure</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Structure moléculaire</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Salicinoids are phenolic glycosides (PGs) characteristic of the Salicaceae and are known defenses against insect herbivory. Common examples are salicin, salicortin, tremuloidin, and tremulacin, which accumulate to high concentrations in the leaves and bark of willows and poplars. Although their biosynthetic pathway is not known, recent work has suggested that benzyl benzoate may be a potential biosynthetic intermediate. Two candidate genes, named PtACT47 and PtACT49, encoding BAHD-type acyl transferases were identified and are predicted to produce such benzylated secondary metabolites. Herein described are the cDNA cloning, heterologous expression and in vitro functional characterization of these two BAHD acyltransferases. Recombinant PtACT47 exhibited low substrate selectivity and could utilize acetyl-CoA, benzoyl-CoA, and cinnamoyl-CoA as acyl donors with a variety of alcohols as acyl acceptors. This enzyme showed the greatest Km/Kcat ratio (45.8 nM(-1) s(-1)) and lowest Km values (45.1 μM) with benzoyl-CoA and salicyl alcohol, and was named benzoyl-CoA: salicyl alcohol O-benzoyltransferase (PtSABT). Recombinant PtACT49 utilized a narrower range of substrates, including benzoyl-CoA and acetyl-CoA and a limited number of alcohols. Its highest Km/Kcat (31.8 nM(-1) s(-1)) and lowest Km (55.3 μM) were observed for benzoyl-CoA and benzyl alcohol, and it was named benzoyl-CoA: benzyl alcohol O-benzoyltransferase (PtBEBT). Both enzymes were also capable of synthesizing plant volatile alcohol esters, such as hexenyl benzoate, at trace levels. Although the activities demonstrated are consistent with roles in salicinoid biosynthesis, direct tests of this hypothesis using transgenic poplar must still be performed.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25561400</PMID><DateCompleted><Year>2016</Year><Month>01</Month><Day>19</Day></DateCompleted><DateRevised><Year>2017</Year><Month>11</Month><Day>16</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1873-3700</ISSN><JournalIssue CitedMedium="Internet"><Volume>113</Volume><PubDate><Year>2015</Year><Month>May</Month></PubDate></JournalIssue><Title>Phytochemistry</Title><ISOAbbreviation>Phytochemistry</ISOAbbreviation></Journal><ArticleTitle>Functional characterization of two acyltransferases from Populus trichocarpa capable of synthesizing benzyl benzoate and salicyl benzoate, potential intermediates in salicinoid phenolic glycoside biosynthesis.</ArticleTitle><Pagination><MedlinePgn>149-59</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.phytochem.2014.10.018</ELocationID><ELocationID EIdType="pii" ValidYN="Y">S0031-9422(14)00422-1</ELocationID><Abstract><AbstractText>Salicinoids are phenolic glycosides (PGs) characteristic of the Salicaceae and are known defenses against insect herbivory. Common examples are salicin, salicortin, tremuloidin, and tremulacin, which accumulate to high concentrations in the leaves and bark of willows and poplars. Although their biosynthetic pathway is not known, recent work has suggested that benzyl benzoate may be a potential biosynthetic intermediate. Two candidate genes, named PtACT47 and PtACT49, encoding BAHD-type acyl transferases were identified and are predicted to produce such benzylated secondary metabolites. Herein described are the cDNA cloning, heterologous expression and in vitro functional characterization of these two BAHD acyltransferases. Recombinant PtACT47 exhibited low substrate selectivity and could utilize acetyl-CoA, benzoyl-CoA, and cinnamoyl-CoA as acyl donors with a variety of alcohols as acyl acceptors. This enzyme showed the greatest Km/Kcat ratio (45.8 nM(-1) s(-1)) and lowest Km values (45.1 μM) with benzoyl-CoA and salicyl alcohol, and was named benzoyl-CoA: salicyl alcohol O-benzoyltransferase (PtSABT). Recombinant PtACT49 utilized a narrower range of substrates, including benzoyl-CoA and acetyl-CoA and a limited number of alcohols. Its highest Km/Kcat (31.8 nM(-1) s(-1)) and lowest Km (55.3 μM) were observed for benzoyl-CoA and benzyl alcohol, and it was named benzoyl-CoA: benzyl alcohol O-benzoyltransferase (PtBEBT). Both enzymes were also capable of synthesizing plant volatile alcohol esters, such as hexenyl benzoate, at trace levels. Although the activities demonstrated are consistent with roles in salicinoid biosynthesis, direct tests of this hypothesis using transgenic poplar must still be performed.</AbstractText><CopyrightInformation>Copyright © 2014 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Chedgy</LastName><ForeName>Russell J</ForeName><Initials>RJ</Initials><AffiliationInfo><Affiliation>Centre for Forest Biology, Department of Biology, University of Victoria, P.O. Box 3020, STN CSC, Victoria, BC V8W 3N5, Canada.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Köllner</LastName><ForeName>Tobias G</ForeName><Initials>TG</Initials><AffiliationInfo><Affiliation>Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, 07745 Jena, Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Constabel</LastName><ForeName>C Peter</ForeName><Initials>CP</Initials><AffiliationInfo><Affiliation>Centre for Forest Biology, Department of Biology, University of Victoria, P.O. Box 3020, STN CSC, Victoria, BC V8W 3N5, Canada. Electronic address: cpc@uvic.ca.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2015</Year><Month>01</Month><Day>02</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Phytochemistry</MedlineTA><NlmUniqueID>0151434</NlmUniqueID><ISSNLinking>0031-9422</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000214">Acyl Coenzyme A</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001565">Benzoates</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001592">Benzyl Alcohols</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D018076">DNA, Complementary</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005960">Glucosides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D006027">Glycosides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010636">Phenols</NameOfSubstance></Chemical><Chemical><RegistryNumber>29836-40-6</RegistryNumber><NameOfSubstance UI="C095421">tremulacin</NameOfSubstance></Chemical><Chemical><RegistryNumber>4649620TBZ</RegistryNumber><NameOfSubstance UI="C005696">salicin</NameOfSubstance></Chemical><Chemical><RegistryNumber>6756-74-7</RegistryNumber><NameOfSubstance UI="C037817">benzoyl-coenzyme A</NameOfSubstance></Chemical><Chemical><RegistryNumber>76109-04-1</RegistryNumber><NameOfSubstance UI="C022903">cinnamoyl-coenzyme A</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.3.-</RegistryNumber><NameOfSubstance UI="D000217">Acyltransferases</NameOfSubstance></Chemical><Chemical><RegistryNumber>FA1N0842KB</RegistryNumber><NameOfSubstance UI="C010631">salicyl alcohol</NameOfSubstance></Chemical><Chemical><RegistryNumber>N863NB338G</RegistryNumber><NameOfSubstance UI="C006723">benzyl benzoate</NameOfSubstance></Chemical><Chemical><RegistryNumber>YI29948E0Q</RegistryNumber><NameOfSubstance UI="C113068">salicortin</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000214" MajorTopicYN="N">Acyl Coenzyme A</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D000217" MajorTopicYN="N">Acyltransferases</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001565" MajorTopicYN="N">Benzoates</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001592" MajorTopicYN="N">Benzyl Alcohols</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D018076" MajorTopicYN="N">DNA, Complementary</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004926" MajorTopicYN="N">Escherichia coli</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005960" MajorTopicYN="N">Glucosides</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006027" MajorTopicYN="N">Glycosides</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010636" MajorTopicYN="N">Phenols</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D018515" MajorTopicYN="N">Plant Leaves</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D032107" MajorTopicYN="N">Populus</DescriptorName><QualifierName UI="Q000201" MajorTopicYN="Y">enzymology</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Benzoyltransferase</Keyword><Keyword MajorTopicYN="N">Escherichia coli heterologous expression</Keyword><Keyword MajorTopicYN="N">Herbivore defense</Keyword><Keyword MajorTopicYN="N">Poplar</Keyword><Keyword MajorTopicYN="N">Populus trichocarpa</Keyword><Keyword MajorTopicYN="N">Salicaceae</Keyword><Keyword MajorTopicYN="N">Salicinoid phenolic glycosides</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2014</Year><Month>06</Month><Day>30</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2014</Year><Month>10</Month><Day>07</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2014</Year><Month>10</Month><Day>16</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>1</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>1</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2016</Year><Month>1</Month><Day>20</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25561400</ArticleId><ArticleId IdType="pii">S0031-9422(14)00422-1</ArticleId><ArticleId IdType="doi">10.1016/j.phytochem.2014.10.018</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Allemagne</li><li>Canada</li></country></list><tree><country name="Canada"><noRegion><name sortKey="Chedgy, Russell J" sort="Chedgy, Russell J" uniqKey="Chedgy R" first="Russell J" last="Chedgy">Russell J. Chedgy</name></noRegion><name sortKey="Constabel, C Peter" sort="Constabel, C Peter" uniqKey="Constabel C" first="C Peter" last="Constabel">C Peter Constabel</name></country><country name="Allemagne"><noRegion><name sortKey="Kollner, Tobias G" sort="Kollner, Tobias G" uniqKey="Kollner T" first="Tobias G" last="Köllner">Tobias G. Köllner</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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