{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1361699994417824384.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/anie.201909407"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.201909407"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201909407"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.201909407"}}],"dc:title":[{"@value":"Cu<sup>II</sup>‐Containing 1‐Aminocyclopropane Carboxylic Acid Oxidase Is an Efficient Stereospecific Diels–Alderase"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>In the context of developing ecofriendly chemistry, artificial enzymes are now considered as promising tools for synthesis. They are prepared in particular with the aim to catalyze reactions that are rarely, if ever, catalyzed by natural enzymes. We discovered that 1‐aminocyclopropane carboxylic acid oxidase reconstituted with Cu<jats:sup>II</jats:sup> served as an efficient artificial Diels–Alderase. The kinetic parameters of the catalysis of the cycloaddition of cyclopentadiene and 2‐azachalcone were determined (<jats:italic>K</jats:italic><jats:sub>M</jats:sub>=230 μ<jats:sc>m</jats:sc>, <jats:italic>k</jats:italic><jats:sub>app</jats:sub>=3 h<jats:sup>−1</jats:sup>), which gave access to reaction conditions that provided quantitative yield and >99 % <jats:italic>ee</jats:italic> of the (<jats:italic>1S</jats:italic>,<jats:italic>2R</jats:italic>,<jats:italic>3R</jats:italic>,<jats:italic>4R</jats:italic>) product isomer. This unprecedented performance was rationalized by molecular modeling as only one docking pose of 2‐azachalcone was possible in the active site of the enzyme and this was the one that leads to the (<jats:italic>1S</jats:italic>,<jats:italic>2R</jats:italic>,<jats:italic>3R</jats:italic>,<jats:italic>4R</jats:italic>) product isomer.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1381699994417824387","@type":"Researcher","foaf:name":[{"@value":"Wadih Ghattas"}],"jpcoar:affiliationName":[{"@value":"Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR 8182 CNRS – Univ Paris Sud Université Paris-Saclay  Orsay 91405 Cedex France"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994417824388","@type":"Researcher","foaf:name":[{"@value":"Virginie Dubosclard"}],"jpcoar:affiliationName":[{"@value":"Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR 8182 CNRS – Univ Paris Sud Université Paris-Saclay  Orsay 91405 Cedex France"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994417824385","@type":"Researcher","foaf:name":[{"@value":"Sybille Tachon"}],"jpcoar:affiliationName":[{"@value":"Institut des Sciences Moléculaires de Marseille (iSm2), UMR 7313 CNRS – Aix Marseille Univ Centrale Marseille  Marseille 13013 Cedex France"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994417824390","@type":"Researcher","foaf:name":[{"@value":"Morane Beaumet"}],"jpcoar:affiliationName":[{"@value":"Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR 8182 CNRS – Univ Paris Sud Université Paris-Saclay  Orsay 91405 Cedex France"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994417824384","@type":"Researcher","foaf:name":[{"@value":"Régis Guillot"}],"jpcoar:affiliationName":[{"@value":"Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR 8182 CNRS – Univ Paris Sud Université Paris-Saclay  Orsay 91405 Cedex France"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994417824386","@type":"Researcher","foaf:name":[{"@value":"Marius Réglier"}],"jpcoar:affiliationName":[{"@value":"Institut des Sciences Moléculaires de Marseille (iSm2), UMR 7313 CNRS – Aix Marseille Univ Centrale Marseille  Marseille 13013 Cedex France"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994417824389","@type":"Researcher","foaf:name":[{"@value":"A. Jalila Simaan"}],"jpcoar:affiliationName":[{"@value":"Institut des Sciences Moléculaires de Marseille (iSm2), UMR 7313 CNRS – Aix Marseille Univ Centrale Marseille  Marseille 13013 Cedex France"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994417824391","@type":"Researcher","foaf:name":[{"@value":"Jean‐Pierre Mahy"}],"jpcoar:affiliationName":[{"@value":"Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR 8182 CNRS – Univ Paris Sud Université Paris-Saclay  Orsay 91405 Cedex France"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"14337851"},{"@type":"EISSN","@value":"15213773"}],"prism:publicationName":[{"@value":"Angewandte Chemie International Edition"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2019-09-05","prism:volume":"58","prism:number":"41","prism:startingPage":"14605","prism:endingPage":"14609"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.201909407"},{"@id":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201909407"},{"@id":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.201909407"}],"createdAt":"2019-09-05","modifiedAt":"2023-09-03","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360005514496086912","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Cupin Variants as a Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes"}]},{"@id":"https://cir.nii.ac.jp/crid/1360290617849264256","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Incorporation of a Cp*Rh(III)-dithiophosphate Cofactor with Latent Activity into a Protein Scaffold Generates a Biohybrid Catalyst Promoting C(sp<sup>2</sup>)–H Bond Functionalization"}]},{"@id":"https://cir.nii.ac.jp/crid/1360861707156460416","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"An artificial metallolyase with pliable 2-His-1-carboxylate facial triad for stereoselective Michael addition"}]},{"@id":"https://cir.nii.ac.jp/crid/2050870367081136768","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Exploring and adapting the molecular selectivity of artificial metalloenzymes"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/anie.201909407"},{"@type":"CROSSREF","@value":"10.1002/anie.202000129_references_DOI_1EFTerFD2lhFRrlScEeInLfgRfL"},{"@type":"CROSSREF","@value":"10.1246/bcsj.20200316_references_DOI_1EFTerFD2lhFRrlScEeInLfgRfL"},{"@type":"CROSSREF","@value":"10.1021/acs.inorgchem.0c02245_references_DOI_1EFTerFD2lhFRrlScEeInLfgRfL"},{"@type":"CROSSREF","@value":"10.1039/d2sc06809e_references_DOI_1EFTerFD2lhFRrlScEeInLfgRfL"}]}