Relative Performance of Alkynes in Copper-Catalyzed Azide–Alkyne Cycloaddition

Copper-catalyzed azide–alkyne cycloaddition (CuAAC) has found numerous applications in a variety of fields. We report here only modest differences in the reactivity of various classes of terminal alkynes under typical bioconjugative and preparative organic conditions. Propargyl compounds represent a...

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Bibliographic Details
Published in:Bioconjugate chemistry 2013-04, Vol.24 (4), p.684-689
Main Authors: Kislukhin, Alexander A, Hong, Vu P, Breitenkamp, Kurt E, Finn, M. G
Format: Article
Language:English
Subjects:
Alcohols - chemical synthesis
Alcohols - chemistry
Alkynes - chemistry
Azides - chemical synthesis
Azides - chemistry
Catalysis
Catalysts
Chemical compounds
Copper
Copper - chemistry
Cyclization
Molecular Structure
Optimization
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Summary:Copper-catalyzed azide–alkyne cycloaddition (CuAAC) has found numerous applications in a variety of fields. We report here only modest differences in the reactivity of various classes of terminal alkynes under typical bioconjugative and preparative organic conditions. Propargyl compounds represent an excellent combination of azide reactivity, ease of installation, and cost. Electronically activated propiolamides are slightly more reactive, at the expense of increased propensity for Michael addition. Certain alkynes, including tertiary propargyl carbamates, are not suitable for bioconjugation due to copper-induced fragmentation. A fluorogenic probe based on such reactivity is available in one step from rhodamine 110 and can be useful for optimization of CuAAC conditions.
ISSN:1043-1802
1520-4812
DOI:10.1021/bc300672b