{"@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/1390282679097002880.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1246/bcsj.72.1377"}},{"identifier":{"@type":"NDL_BIB_ID","@value":"4765241"}},{"identifier":{"@type":"URI","@value":"http://id.ndl.go.jp/bib/4765241"}},{"identifier":{"@type":"URI","@value":"https://ndlsearch.ndl.go.jp/books/R000000004-I4765241"}},{"identifier":{"@type":"URI","@value":"https://academic.oup.com/bcsj/article-pdf/72/6/1377/56199496/bcsj.72.1377.pdf"}},{"identifier":{"@type":"DOI","@value":"10.1002/chin.199949198"}},{"identifier":{"@type":"NAID","@value":"130004150386"}},{"identifier":{"@type":"NAID","@value":"10009151145"}}],"dc:title":[{"@language":"en","@value":"A Divergent Synthesis of Lipid A and Its Chemically Stable Unnatural Analogues."},{"@language":"ja-Kana","@value":"Divergent Synthesis of Lipid A and Its Chemically Stable Unnatural Analogues"}],"dc:language":"en","description":[{"type":"abstract","notation":[{"@language":"en","@value":"Lipid A and its two chemically stable analogues, wherein the glycosidic phosphoryl groups in lipid A is replaced with 2-(phosphonooxy)ethyl or carboxymethyl groups, have been synthesized by an improved and divergent route via a common allyl glycoside intermediate in which the 4-hydroxy group was protected as a benzyl ether. The total yields were more than 20% for 11 or 12 steps starting from allyl 4,6-<i>O</i>-benzylidene-2-deoxy-2-(trichloroethoxycarbonylamino)-<FONT SIZE=\"-2\">D</FONT>-glucopyranoside. These synthetic chemically stable analogues induce interleukin-6 and tumor necrosis factor <i>α</i> in human peripheral whole blood cells with potencies comparable to those by natural-type synthetic lipid A. The <i>Limulus</i> activities of both analogues were found to be even stronger than the activity of the natural-type one."}],"abstractLicenseFlag":"disallow"}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1410282679097002884","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000000801716"},{"@type":"NRID","@value":"9000256020204"},{"@type":"NRID","@value":"9000256018583"}],"foaf:name":[{"@language":"en","@value":"Liu Wen-Chi"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Department of Chemistry, Graduate School of Science, Osaka 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エイゴブン"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282679096740480","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Synthesis and Biological Activities of Lipid A Analogs Possessing .BETA.-Glycosidic Linkage at 1-Position."},{"@value":"Synthesis and Biological Activities of Lipid A Analogs Possessing <i>β</i>-Glycosidic Linkage at 1-Position"},{"@value":"Synthesis and Biological Activities of Lipid A Analogues Possessing β‐Glycosidic Linkage at 1‐Position."},{"@value":"Synthesis and biological activities of lipid A analogs possessing β-glycosidic linkage at 1-position"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282679098106880","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Synthesis of [3H]-Labeled Bioactive Lipid A Analogs and Their Use for Detection of Lipid A-Binding Proteins on Murine Macrophages."}]},{"@id":"https://cir.nii.ac.jp/crid/1390282679118915456","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Synthesis of Rubrivivax gelatinosus Lipid A and Analogues for Investigation of the Structural Basis for Immunostimulating and Inhibitory Activities"},{"@value":"Synthesis of <i>Rubrivivax gelatinosus</i> Lipid A and Analogues for Investigation of the Structural Basis for Immunostimulating and Inhibitory Activities"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282679123999872","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Key structures of bacterial peptidoglycan and lipopolysaccharide triggering the innate immune system of higher animals: Chemical synthesis and functional studies"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282679135058560","@type":"Article","resourceType":"学術雑誌論文(journal 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