Relative performance of alkynes in copper-catalyzed azide-alkyne cycloaddition.
Relative performance of alkynes in copper-catalyzed azide-alkyne cycloaddition.
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DOI：
10.1021/bc300672b
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发表时间：
2013-04-17
影响因子：
4.7
通讯作者：
Finn MG
中科院分区：
文献类型：
--
作者：
Kislukhin AA;Hong VP;Breitenkamp KE;Finn MG
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.
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