{"@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/1360846644032467200.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1246/bcsj.58.1200"}},{"identifier":{"@type":"URI","@value":"https://academic.oup.com/bcsj/article-pdf/58/4/1200/55707023/bcsj.58.1200.pdf"}},{"identifier":{"@type":"NAID","@value":"130001983779"}}],"dc:title":[{"@value":"Copper(II)-Catalyzed Transamination between Pyruvate and Hydrophobic Pyridoxamine Embedded in Synthetic Bilayer Membranes"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title>\n               <jats:p>The copper(II)-catalyzed transamination of 4-aminomethyl-5-[(dihexadecylamino)methyl]-2-methyl-3-pyridinol [(PM)2C16] with sodium pyruvate was investigated in an aqueous medium at pH 6.9, μ 0.10 (KCl), and 30.0±0.1 °C in the presence of single-walled bilayer vesicles of N,N-dihexadecyl-Nα-[6-(trimethylammonio)hexanoyl]-l-alaninamide bromide [N+C5Ala2C16] and N,N-dihexadecyl-Nα-[6-(trimethylammonio)hexanoyl]-l-histidinamide bromide [N+C5His2C16]. The binding mode of the pyridoxamine moiety in the vesicles was clarified by comparing the reaction behavior of the (PM)2C16–pyruvate–CuII system with that of the 4-aminomethyl-5-dodecylthiomethyl-2-methyl-3-pyridinol [(PM)C12]–pyruvate–CuII system. The pyridoxamine moiety of (PM)2C16 was more tightly anchored in the hydrogen-belt domain of the membranes than that of (PM)C12 as confirmed by fluorescence polarization spectroscopy. The difference in binding mode between (PM)2C16 and (PM)C12 is reflected on the copper(II)-coordination equilibria for the formation of the copper(II)–ketimine intermediates. The copper(II)-catalyzed transamination of (PM)2C16 with pyruvate in the N+C5His2C16 vesicle was most enhanced among related reaction systems treated here. The rate enhancement was attributed to the favorable formation of the reactive 2:1 ketimine–copper(II) chelate and the general-base catalysis by the coordination-free imidazolyl group of the lipid.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1583105977572463874","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000021850068"}],"foaf:name":[{"@value":"Yukito Murakami"}],"jpcoar:affiliationName":[{"@value":"Department of Organic Synthesis, Faculty of Engineering, Kyushu University"}]},{"@id":"https://cir.nii.ac.jp/crid/1583105977572463873","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000021850070"}],"foaf:name":[{"@value":"Jun-ichi Kikuchi"}],"jpcoar:affiliationName":[{"@value":"Department of Organic Synthesis, Faculty of Engineering, Kyushu University"}]},{"@id":"https://cir.nii.ac.jp/crid/1583105977572463872","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000021850072"}],"foaf:name":[{"@value":"Kazunari Akiyoshi"}],"jpcoar:affiliationName":[{"@value":"Department of Organic Synthesis, Faculty of Engineering, Kyushu University"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00092673"},{"@type":"EISSN","@value":"13480634"}],"prism:publicationName":[{"@value":"Bulletin of the Chemical Society of Japan"}],"dc:publisher":[{"@value":"Oxford University Press (OUP)"}],"prism:publicationDate":"1985-04-01","prism:volume":"58","prism:number":"4","prism:startingPage":"1200","prism:endingPage":"1204"},"reviewed":"false","dcterms:accessRights":"http://purl.org/coar/access_right/c_abf2","dc:rights":["https://academic.oup.com/pages/standard-publication-reuse-rights"],"url":[{"@id":"https://academic.oup.com/bcsj/article-pdf/58/4/1200/55707023/bcsj.58.1200.pdf"}],"createdAt":"2006-07-26","modifiedAt":"2024-01-18","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360002219108891648","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Enantioselective Catalysis Performed by Bilayer-type Artificial Aminotransferase. Effect of a Chiral Binaphthol Moiety Placed in the Reaction Site"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011146246785536","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Photochemical probes for model membrane structures"}]},{"@id":"https://cir.nii.ac.jp/crid/1360565169056589184","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Substrate Selectivity of Artificial Transaminase Constituted with Functionalized Bilayer Membrane"}]},{"@id":"https://cir.nii.ac.jp/crid/1360565169056798976","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Functionalized Bilayer Membranes as Artificial Tryptophan Synthase. Characterization of Catalytic Efficiency, Substrate Specificity, and Reaction Selectivity"}]},{"@id":"https://cir.nii.ac.jp/crid/1360565169062230528","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Stereoselective Synthesis of β-Phenylserine from Glycine and Benzaldehyde as Mediated by Catalytic Bilayer Membranes, Artificial Vitamin B6-dependent Enzymes"}]},{"@id":"https://cir.nii.ac.jp/crid/1360565169062303232","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Enantioselective Catalysis by Supramolecular Bilayer Membrane as Artificial Aminotransferase"}]},{"@id":"https://cir.nii.ac.jp/crid/1360574095473291648","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Preparation of stable single-compartment vesicles with cationic and zwitterionic amphiphiles involving amino acid residues"}]},{"@id":"https://cir.nii.ac.jp/crid/1360846644031946368","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Catalytic Efficiency of Functionalized Vesicles in the Transamination of Pyridoxal-5′-phosphate with a Hydrophobic Amino Acid"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137045678481280","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Bilayer induced diastereomeric kinetic differentiation"}]},{"@id":"https://cir.nii.ac.jp/crid/1361418521106152064","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Characterization of molecular aggregates of peptide amphiphiles and kinetics of dynamic processes performed by single-walled vesicles"}]},{"@id":"https://cir.nii.ac.jp/crid/1362262946415001216","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Phase separation and reactivity changes of phenyl ester substrate and imidazole catalyst in the dialkylammonium bilayer membrane"}]},{"@id":"https://cir.nii.ac.jp/crid/1362544420308601472","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Functionalized vesicular assembly. Enantioselective catalysis of ester hydrolysis"}]},{"@id":"https://cir.nii.ac.jp/crid/1363107368534163840","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"The Effect of Solvent on Spectra. I. A New Empirical Measure of Solvent Polarity: Z-Values"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001204121300480","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Aggregate morphology and hydrogenation reactivity of functionalized bilayer membrane composed of peptide lipid having NADH activity."}]},{"@id":"https://cir.nii.ac.jp/crid/1390001204123048704","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Copper(II)-catalyzed transamination of hydrophobic pyridoxamine with pyruvic acid in functionalized bilayer vesicles."}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1246/bcsj.58.1200"},{"@type":"CIA","@value":"130001983779"},{"@type":"OPENAIRE","@value":"doi_dedup___::19d821e6b4d20c34fa06cf7b584c0c6d"},{"@type":"CROSSREF","@value":"10.1246/cl.1994.1701_references_DOI_J4Kx0uS4r1PykIpMgFXzHtK9aNL"},{"@type":"CROSSREF","@value":"10.1246/bcsj.63.2339_references_DOI_J4Kx0uS4r1PykIpMgFXzHtK9aNL"},{"@type":"CROSSREF","@value":"10.1246/cl.1994.1559_references_DOI_J4Kx0uS4r1PykIpMgFXzHtK9aNL"},{"@type":"CROSSREF","@value":"10.1246/cl.1993.553_references_DOI_J4Kx0uS4r1PykIpMgFXzHtK9aNL"},{"@type":"CROSSREF","@value":"10.1246/bcsj.62.2045_references_DOI_J4Kx0uS4r1PykIpMgFXzHtK9aNL"}]}