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Statements

Subject Item
dbr:Macrophomic_acid
rdf:type
yago:PhysicalEntity100001930 yago:BenzoicAcid114775321 yago:Substance100019613 yago:Part113809207 yago:WikicatAromaticKetones owl:Thing yago:Material114580897 wikidata:Q11173 yago:CarboxylicAcid114739360 yago:Element114840755 yago:Acid114607521 yago:Relation100031921 yago:WikicatDicarboxylicAcids yago:OrganicCompound114727670 yago:Compound114818238 yago:WikicatBenzoicAcids dbo:ChemicalCompound yago:Chemical114806838 umbel-rc:ChemicalSubstanceType yago:Abstraction100002137 n26:ChemicalObject yago:Matter100020827 yago:Ketone114926294 dbo:ChemicalSubstance yago:Quintessence114847103 yago:WikicatPhenolEthers
rdfs:label
Macrophomic acid
rdfs:comment
Macrophomic acid is a fungal metabolite isolated from the fungus . The enzyme converts 5-acetyl-4-methoxy-6-methyl-2-pyrone to 4-acetyl-3-methoxy-5-methyl-benzoic acid (macrophomic acid) through an unusual intermolecular Diels-Alder reaction (Scheme 1). The pathway to formation of macrophomic acid suggests that the enzyme is a natural Diels-Alderase. Formation of this type of aromatic ring compound normally proceeds via the shikimate and polyketide pathways; however, the production of macrophomic acid by macrophomate synthase proceeds totally differently. Learning about the production of macrophomic acid by a possible natural Diels-Alderase enzyme is important in understanding enzyme catalytic mechanisms. This knowledge can then be applied to organic synthesis.
foaf:depiction
n12:macrophomic_acid.svg n12:Oxaloacetate_enolate_formation.gif n12:Diels-alder_mechanism.png n12:Scheme_1_macrophomic_acid.gif n12:Scheme_2_macrophomic_acid.gif
dcterms:subject
dbc:Aromatic_ketones dbc:Methoxy_compounds dbc:Acetophenones dbc:Benzoic_acids dbc:Phenol_ethers dbc:Carboxylic_acids
dbo:wikiPageID
23184842
dbo:wikiPageRevisionID
1042908354
dbo:wikiPageWikiLink
dbc:Aromatic_ketones dbr:Aldol_condensation dbr:Active_site dbc:Methoxy_compounds dbc:Benzoic_acids dbr:Polyketide dbc:Acetophenones dbr:Fungus dbr:Michael_reaction n20:Oxaloacetate_enolate_formation.gif dbr:Enzyme n20:Scheme_1_macrophomic_acid.gif n20:Scheme_2_macrophomic_acid.gif n20:Diels-alder_mechanism.png dbr:Enol dbr:Macrophoma_commelinae dbc:Phenol_ethers dbr:Macrophomate_synthase dbr:Diels-Alder_reaction dbr:Metabolite dbr:Aromaticity dbc:Carboxylic_acids dbr:Shikimic_acid
owl:sameAs
wikidata:Q6725521 n16:ماکروفومیک_اسید yago-res:Macrophomic_acid dbpedia-sh:Makrofominska_kiselina n21:4qpRh freebase:m.064kx_3 dbpedia-sr:Makrofominska_kiselina dbpedia-fa:ماکروفومیک_اسید
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dbt:Stdinchicite dbt:Chembox_Hazards dbt:Chembox_Identifiers dbt:Chembox dbt:Chembox_Properties dbt:Fdacite dbt:Cascite dbt:Chemspidercite dbt:Ebicite
dbo:thumbnail
n12:macrophomic_acid.svg?width=300
dbp:imagefile
macrophomic acid.svg
dbp:imagesize
200
dbp:pin
4
dbp:systematicname
4
dbp:verifiedfields
changed
dbp:verifiedrevid
422660555
dbp:watchedfields
changed
dbo:abstract
Macrophomic acid is a fungal metabolite isolated from the fungus . The enzyme converts 5-acetyl-4-methoxy-6-methyl-2-pyrone to 4-acetyl-3-methoxy-5-methyl-benzoic acid (macrophomic acid) through an unusual intermolecular Diels-Alder reaction (Scheme 1). The pathway to formation of macrophomic acid suggests that the enzyme is a natural Diels-Alderase. Formation of this type of aromatic ring compound normally proceeds via the shikimate and polyketide pathways; however, the production of macrophomic acid by macrophomate synthase proceeds totally differently. Learning about the production of macrophomic acid by a possible natural Diels-Alderase enzyme is important in understanding enzyme catalytic mechanisms. This knowledge can then be applied to organic synthesis.
gold:hypernym
dbr:Metabolite
prov:wasDerivedFrom
wikipedia-en:Macrophomic_acid?oldid=1042908354&ns=0
dbo:wikiPageLength
5933
dbo:iupacName
4-Ethanoyl-3-methoxy-5-methylbenzenecarboxylic acid 4-Acetyl-3-methoxy-5-methylbenzoic acid
foaf:isPrimaryTopicOf
wikipedia-en:Macrophomic_acid