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

Cited 21 time in scopus
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Title
Optimizing the selectivity of DIFO-based reagents for intracellular bioorthogonal applications
Author(s)
E J Kim; D W Kang; H F Leucke; M R Bond; S Ghosh; D C Love; Jong Seog Ahn; D O Kang; J A Hanover
Bibliographic Citation
Carbohydrate Research, vol. 377, pp. 18-27
Publication Year
2013
Abstract
One 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.
Keyword
Copper-catalyzed azide-alkyneCycloadditionGlycoconjugatesO-GlcNAcStrain-promoted azide-alkyne cycloaddition
ISSN
0008-6215
Publisher
Elsevier
DOI
http://dx.doi.org/10.1016/j.carres.2013.05.014
Type
Article
Appears in Collections:
Ochang Branch Institute > Anticancer Agent Research Center > 1. Journal Articles
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