Optimizing the selectivity of DIFO-based reagents for intracellular bioorthogonal applications

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dc.contributor.authorE J Kim-
dc.contributor.authorD W Kang-
dc.contributor.authorH F Leucke-
dc.contributor.authorM R Bond-
dc.contributor.authorS Ghosh-
dc.contributor.authorD C Love-
dc.contributor.authorJong Seog Ahn-
dc.contributor.authorD O Kang-
dc.contributor.authorJ A Hanover-
dc.date.accessioned2017-04-19T09:45:48Z-
dc.date.available2017-04-19T09:45:48Z-
dc.date.issued2013-
dc.identifier.issn0008-6215-
dc.identifier.uri10.1016/j.carres.2013.05.014ko
dc.identifier.urihttps://oak.kribb.re.kr/handle/201005/11625-
dc.description.abstractOne of the most commonly employed bioorthogonal reactions with azides is copper-catalyzed azide-alkyne [3+2] cycloaddition (CuAAC, a 'click' reaction). More recently, the strain-promoted azide-alkyne [3+2] cycloaddition (SPAAC, a copper-free 'click' reaction) was developed, in which an alkyne is sufficiently strained to promote rapid cycloaddition with an azide to form a stable triazole conjugate. In this report, we show that an internal alkyne in a strained ring system with two electron-withdrawing fluorine atoms adjacent to the carbon-carbon triple bond reacts to yield covalent adducts not only with azide moieties but also reacts with free sulfhydryl groups abundant in the cytosol. We have identified conditions that allow the enhanced reactivity to be tolerated when using such conformationally strained reagents to enhance reaction rates and selectivity for bioorthogonal applications such as O-GlcNAc detection.-
dc.publisherElsevier-
dc.titleOptimizing the selectivity of DIFO-based reagents for intracellular bioorthogonal applications-
dc.title.alternativeOptimizing the selectivity of DIFO-based reagents for intracellular bioorthogonal applications-
dc.typeArticle-
dc.citation.titleCarbohydrate Research-
dc.citation.number0-
dc.citation.endPage27-
dc.citation.startPage18-
dc.citation.volume377-
dc.contributor.affiliatedAuthorJong Seog Ahn-
dc.contributor.alternativeName김은-
dc.contributor.alternativeName강동-
dc.contributor.alternativeNameLeucke-
dc.contributor.alternativeNameBond-
dc.contributor.alternativeNameGhosh-
dc.contributor.alternativeNameLove-
dc.contributor.alternativeName안종석-
dc.contributor.alternativeName강대욱-
dc.contributor.alternativeNameHanover-
dc.identifier.bibliographicCitationCarbohydrate Research, vol. 377, pp. 18-27-
dc.identifier.doi10.1016/j.carres.2013.05.014-
dc.subject.keywordCopper-catalyzed azide-alkyne-
dc.subject.keywordCycloaddition-
dc.subject.keywordGlycoconjugates-
dc.subject.keywordO-GlcNAc-
dc.subject.keywordStrain-promoted azide-alkyne cycloaddition-
dc.subject.localCopper-catalyzed azide-alkyne-
dc.subject.localCycloaddition-
dc.subject.localGlycoconjugates-
dc.subject.localO-GlcNAc-
dc.subject.localStrain-promoted azide-alkyne cycloaddition-
dc.description.journalClassY-
Appears in Collections:
Ochang Branch Institute > Chemical Biology Research Center > 1. Journal Articles
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