lFacile quenching and spatial patterning of cylooctynes via strain-promoted alkyne–azide cycloaddition of inorganic azides

Little is known about the reactivity of strain-promoted alkyne–azide cycloaddition (SPAAC) reagents with inorganic azides. We explore the reactions of a variety of popular SPAAC reagents with sodium azide and hydrozoic acid. We find that the reactions proceed in water at rates comparable to those wi...

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Published inBioconjugate chemistry Vol. 28; no. 5; pp. 1560 - 1565
Main Authors Bjerknes, Matthew, Cheng, Hazel, McNitt, Christopher D., Popik, Vladimir V.
Format Journal Article
LanguageEnglish
Published 09.05.2017
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Summary:Little is known about the reactivity of strain-promoted alkyne–azide cycloaddition (SPAAC) reagents with inorganic azides. We explore the reactions of a variety of popular SPAAC reagents with sodium azide and hydrozoic acid. We find that the reactions proceed in water at rates comparable to those with organic azides, yielding in all cases a triazole adduct. The azide ion’s utility as a cyclooctyne quenching reagent is demonstrated by using it to spatially pattern uniformly-doped hydrogels. The facile quenching of cyclooctynes demonstrated here should be useful in other bioorthogonal ligation techniques in which cyclooctynes are employed, including SPANC, Diels-Alder, and thiol-yne.
ISSN:1043-1802
1520-4812
DOI:10.1021/acs.bioconjchem.7b00201