{"@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/1362825895108582272.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/cbic.201402030"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcbic.201402030"}},{"identifier":{"@type":"URI","@value":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/cbic.201402030"}}],"dc:title":[{"@value":"Copper‐Free Click Reactions with Polar Bicyclononyne Derivatives for Modulation of Cellular Imaging"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>The ability of cells to incorporate azidosugars metabolically is a useful tool for extracellular glycan labelling. The exposed azide moiety can covalently react with alkynes, such as bicyclo[6.1.0]nonyne (BCN), by strain‐promoted alkyne–azide cycloaddition (SPAAC). However, the use of SPAAC can be hampered by low specificity of the cycloalkyne. In this article we describe the synthesis of more polar BCN derivatives and their properties for selective cellular glycan labelling. The new polar derivatives [amino‐BCN, glutarylamino‐BCN and bis(hydroxymethyl)‐BCN] display reaction rates similar to those of BCN and are less cell‐permeable. The labelling specificity in HEK293 cells is greater than that of BCN, as determined by confocal microscopy and flow cytometry. Interestingly, amino‐BCN appears to be highly specific for the Golgi apparatus. In addition, the polar BCN derivatives label the N‐glycan of the membrane calcium channel TRPV5 in HEK293 cells with significantly enhanced signal‐to‐noise ratios.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1382825895108582276","@type":"Researcher","foaf:name":[{"@value":"E. H. P. Leunissen"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895108582273","@type":"Researcher","foaf:name":[{"@value":"M. H. L. Meuleners"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895108582272","@type":"Researcher","foaf:name":[{"@value":"J. M. M. Verkade"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895108582275","@type":"Researcher","foaf:name":[{"@value":"J. Dommerholt"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895108582274","@type":"Researcher","foaf:name":[{"@value":"J. G. J. Hoenderop"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895108582277","@type":"Researcher","foaf:name":[{"@value":"F. L. van Delft"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"14394227"},{"@type":"EISSN","@value":"14397633"}],"prism:publicationName":[{"@value":"ChemBioChem"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2014-06-05","prism:volume":"15","prism:number":"10","prism:startingPage":"1446","prism:endingPage":"1451"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcbic.201402030"},{"@id":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/cbic.201402030"}],"createdAt":"2014-06-05","modifiedAt":"2025-10-12","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360567183578404864","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Further enhancement of the clickability of doubly sterically-hindered aryl azides by <i>para</i>-amino substitution"}]},{"@id":"https://cir.nii.ac.jp/crid/1520291854860927488","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"90th Commemorative Account : Fascinating Molecules and Reactions : Award Account : Controlled Reactive Intermediates Enabling Facile Molecular Conjugation"}]},{"@id":"https://cir.nii.ac.jp/crid/2050588892097003008","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Effect of resonance on the clickability of alkenyl azides in the strain-promoted cycloaddition with dibenzo-fused cyclooctynes"}]},{"@id":"https://cir.nii.ac.jp/crid/2050870367073706880","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Modular synthesis of unsymmetrical doubly-ring-fused benzene derivatives based on a sequential ring construction strategy using oxadiazinones as a platform molecule"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/cbic.201402030"},{"@type":"CROSSREF","@value":"10.1246/bcsj.20180104_references_DOI_WeEhMSFw0YAhbCXSTw6JyFqmXHw"},{"@type":"CROSSREF","@value":"10.1246/cl.190118_references_DOI_WeEhMSFw0YAhbCXSTw6JyFqmXHw"},{"@type":"CROSSREF","@value":"10.1039/c8cc05791e_references_DOI_WeEhMSFw0YAhbCXSTw6JyFqmXHw"},{"@type":"CROSSREF","@value":"10.1246/cl.190400_references_DOI_WeEhMSFw0YAhbCXSTw6JyFqmXHw"}]}