3,6-Substituted-1,2,4,5-tetrazines: tuning reaction rates for staged labeling applications.

3,6-Substituted-1,2,4,5-tetrazines: tuning reaction rates for staged labeling applications.
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DOI:
10.1039/c4ob00280f
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发表时间:
2014-06-21
影响因子:
3.2
通讯作者:
Wang B
Wang B
中科院分区:
化学3区
文献类型:
--
作者:
Wang D;Chen W;Zheng Y;Dai C;Wang K;Ke B;Wang B

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涉及四嗪的环加成反应已被证明是各种应用的强大生物正交工具。可以想象,使用基于四嗪的反应的顺序和选择性标记可以通过调节反应速率来实现。通过改变四嗪上的取代基,用相同的亲双烯体实现了超过200倍的环加成速率变化。再加上不同的亲二烯体,如异戊烯的可用性,反应速率差异可超过14,000倍。这些取代的四嗪可以在不同条件下用于选择性标记。
Cycloaddition reactions involving tetrazine have proven to be powerful bioorthogonal tools for various applications. Conceivably, sequential and selective labeling using tetrazine-based reactions can be achieved by tuning the reaction rate. By varying the substituents on tetrazine, cycloaddition rate variations of over 200 fold have been achieved with the same dienophile. Coupled with the availability of different dienophiles, such as norbornene, the reaction rate difference can be over 14,000 folds. These substituted tetrazines can be very useful for selective labeling under different conditions.
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