{"@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/1363951794872879360.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/asia.200700305"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fasia.200700305"}},{"identifier":{"@type":"URI","@value":"https://aces.onlinelibrary.wiley.com/doi/pdf/10.1002/asia.200700305"}},{"identifier":{"@type":"PMID","@value":"18219641"}}],"dc:title":[{"@value":"4‐(Dimethylamino)pyridine <i>N</i>‐oxide (DMAPO): An Effective Nucleophilic Catalyst in the Peptide Coupling Reaction with 2‐Methyl‐6‐nitrobenzoic Anhydride"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>Various carboxamides or peptides were synthesized from the corresponding carboxylic acids and amines or α‐amino acids in high yields by the catalysis of 4‐(dimethylamino)pyridine <jats:italic>N</jats:italic>‐oxide (DMAPO) with 2‐methyl‐6‐nitrobenzoic anhydride (MNBA). Because the segment‐coupling reaction of α‐amino acids proceeds through the effective activation of the carboxylic acid moieties with DMAPO in the presence of tertiary amines under mild conditions, undesired racemization was hardly observed in the synthesis of oligopeptides such as Z‐Gly‐Phe‐Val‐OMe, Z‐Phe‐Val‐Ala‐OMe, and Bz‐Val‐Val‐OMe.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1383951794872879361","@type":"Researcher","foaf:name":[{"@value":"Isamu Shiina"}]},{"@id":"https://cir.nii.ac.jp/crid/1383951794872879360","@type":"Researcher","foaf:name":[{"@value":"Hisaya Ushiyama"}]},{"@id":"https://cir.nii.ac.jp/crid/1380298343978144897","@type":"Researcher","foaf:name":[{"@value":"Yo‐ko Yamada"}]},{"@id":"https://cir.nii.ac.jp/crid/1380298343978144896","@type":"Researcher","foaf:name":[{"@value":"Yo‐ichi Kawakita"}]},{"@id":"https://cir.nii.ac.jp/crid/1383951794872879232","@type":"Researcher","foaf:name":[{"@value":"Kenya Nakata"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"18614728"},{"@type":"EISSN","@value":"1861471X"}],"prism:publicationName":[{"@value":"Chemistry – An Asian Journal"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2008-01-29","prism:volume":"3","prism:number":"2","prism:startingPage":"454","prism:endingPage":"461"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fasia.200700305"},{"@id":"https://aces.onlinelibrary.wiley.com/doi/pdf/10.1002/asia.200700305"}],"createdAt":"2008-01-24","modifiedAt":"2025-10-08","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Cyclic%20N-Oxides","dc:title":"Cyclic N-Oxides"},{"@id":"https://cir.nii.ac.jp/all?q=Molecular%20Structure","dc:title":"Molecular Structure"},{"@id":"https://cir.nii.ac.jp/all?q=Nitrobenzoates","dc:title":"Nitrobenzoates"},{"@id":"https://cir.nii.ac.jp/all?q=Oxides","dc:title":"Oxides"},{"@id":"https://cir.nii.ac.jp/all?q=Peptides","dc:title":"Peptides"},{"@id":"https://cir.nii.ac.jp/all?q=Catalysis","dc:title":"Catalysis"},{"@id":"https://cir.nii.ac.jp/all?q=Anhydrides","dc:title":"Anhydrides"}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360002214465363968","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Chemical Synthesis of <i>Helicobacter pylori</i> Lipopolysaccharide Partial Structures and their Selective Proinflammatory Responses"}]},{"@id":"https://cir.nii.ac.jp/crid/1360002216892492160","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines"}]},{"@id":"https://cir.nii.ac.jp/crid/1360004233229726464","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin"}]},{"@id":"https://cir.nii.ac.jp/crid/1360285704859569408","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Organocatalytic Regioselective Chlorosilylation of Oxirane Derivatives: Mild and Effective Insertion of Bulky Silyl Chloride by Using 4‐Methoxypyridine <i>N</i>‐Oxide"}]},{"@id":"https://cir.nii.ac.jp/crid/1360285708125891328","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"A Phosphonium Ylide as an Ionic Nucleophilic Catalyst for Primary Hydroxyl Group Selective Acylation of Diols"}]},{"@id":"https://cir.nii.ac.jp/crid/1360285714737927808","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"An Intramolecular Nucleophile-Catalyzed Aldol-Lactonization (NCAL) Reaction of S-Aryl-(E)-6-oxohex-2-enethioate with N,N-4-Dimethylaminopyridine N-Oxide"}]},{"@id":"https://cir.nii.ac.jp/crid/1360302865739323136","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Synthesis of Bulky <i>N</i>‐Acyl Heterocycles by DMAPO/Boc<sub>2</sub>O‐Mediated One‐Pot Direct <i>N</i>‐Acylation of Less Nucleophilic <i>N</i>‐Heterocycles with α‐Fully Substituted Carboxylic Acids"}]},{"@id":"https://cir.nii.ac.jp/crid/1360302866853654016","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Organocatalytic Regioselective Chloro‐sulfonylation of Mono‐ and 1,2‐Disubstituted Epoxides by Using 4‐Methylpyridine\n                    <i>N</i>\n                    ‐Oxide"}]},{"@id":"https://cir.nii.ac.jp/crid/1360567183134077056","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Esterification via Iron-Catalyzed Activation of Triphenylphosphine with Air"}]},{"@id":"https://cir.nii.ac.jp/crid/1360584339772480256","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"DMAPO/Boc<sub>2</sub>O‐Mediated One‐Pot Direct <i>N</i>1‐Acylation of Indazole with Carboxylic Acids: A Practical Synthesis of <i>N</i>1‐Functionalized Alkyl Indazoles"}]},{"@id":"https://cir.nii.ac.jp/crid/1360848655240537344","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Asymmetric <scp>M</scp>ukaiyama Aldol Reactions Using Chiral Diamine–Coordinated <scp><scp>Sn</scp>(II)</scp> Triflate: Development and Application to Natural Product Synthesis"}]},{"@id":"https://cir.nii.ac.jp/crid/1360848658154095360","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Total Synthesis of AMF-26, an Antitumor Agent for Inhibition of the Golgi System, Targeting ADP-Ribosylation Factor 1"}]},{"@id":"https://cir.nii.ac.jp/crid/1360848658489454592","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"(S)-Stereoisomer of telomestatin as a potent G-quadruplex binder and telomerase inhibitor"}]},{"@id":"https://cir.nii.ac.jp/crid/1360861707383638272","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"DMAPO/Boc<sub>2</sub>O‐Mediated One‐Pot Direct <i>N</i>‐Acylation of Less Nucleophilic <i>N</i>‐Heterocycles with Carboxylic Acids"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282679562934016","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Tetrabenzylpyrophosphate: An Efficient Catalyst for the Synthesis of Carboxamides from Carboxylic Acids and Amines"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282680316829056","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Synthesis of Bacterial Glycoconjugates and Their Bio-functional Studies in Innate Immunity"},{"@language":"ja","@value":"細菌由来複合糖質の合成と自然免疫研究"},{"@language":"ja-Kana","@value":"サイキン ユライ フクゴウ トウシツ ノ ゴウセイ ト シゼン メンエキ ケンキュウ"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282680317571328","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"ja","@value":"テロメスタチンの全合成と類縁体合成"},{"@language":"en","@value":"Total Synthesis of Telomestatin and its Analogues"},{"@language":"ja-Kana","@value":"テロメスタチン ノ ゼン ゴウセイ ト ルイエンタイ ゴウセイ"}]},{"@id":"https://cir.nii.ac.jp/crid/1390863019774281600","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Chemical Synthesis of Lipid A and Its Development as a Vaccine Adjuvant"},{"@language":"ja","@value":"リピドAの化学合成が拓くワクチンアジュバント開発"}]},{"@id":"https://cir.nii.ac.jp/crid/1390869777016566400","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"ja","@value":"迅速脱水縮合剤2-メチル-6-ニトロ安息香酸無水物（MNBA）を用いたエステル化反応の速度論的機構解析および生命科学分野への応用"},{"@language":"en","@value":"Kinetic Mechanistic Study of Expeditious Condensation Agent, 2-Methyl-6-nitrobenzoic Anhydride (MNBA)—Mediated Dehydration Condensation Reactions and Applications to Life Sciences"},{"@language":"ja-Kana","@value":"ジンソク ダッスイ シュクゴウザイ 2-メチル-6-ニトロ アンソク コウサン ムスイブツ(MNBA)オ モチイタ エステルカ ハンノウ ノ ソクドロンテキ キコウ カイセキ オヨビ セイメイ カガク ブンヤ エ ノ オウヨウ"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/asia.200700305"},{"@type":"OPENAIRE","@value":"doi_dedup___::0d61144f3c1728bdb2a4d3ba9cbab5c3"},{"@type":"CROSSREF","@value":"10.1002/chem.201003581_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1039/c5sc03761a_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1246/cl.2008.528_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.5059/yukigoseikyokaishi.82.522_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1002/adsc.201600209_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1021/cs2003824_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1002/adsc.202300487_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1002/slct.202300821_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1021/jm301695c_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1021/jo300139r_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1002/ejoc.202400123_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1002/tcr.201300022_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1039/c0ob00513d_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.3987/com-16-13614_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.5059/yukigoseikyokaishi.70.113_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1002/cctc.202201596_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.5059/yukigoseikyokaishi.84.15_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.5059/yukigoseikyokaishi.73.3_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"},{"@type":"CROSSREF","@value":"10.1021/acscatal.7b02281_references_DOI_IFD1o4tktyy9ElCUzXGCsomifqE"}]}