Journal
BIOCONJUGATE CHEMISTRY
Volume 28, Issue 5, Pages 1560-1565Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.bioconjchem.7b00201
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Funding
- Ontario Genomics under the SPARK program
- National Science Foundation [CHE-1565646]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1565646] Funding Source: National Science Foundation
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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.
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