Chinese Journal of Organic Chemistry >
Aniline Catalysis in Bioconjugations and Material Synthesis
Received date: 2017-08-23
Revised date: 2017-09-28
Online published: 2017-10-11
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21332002, 21561162001) and the Fundamental Research Funds for the Central Universities (No. 20720150046).
The oxime or hydrazone formation is a classic condensation reaction between aldehydes/ketones and hydroxyl amine or hydrazine. It is a simple, yet fundamental coupling reaction that has been widely applied in the ligations and conjugations of biomolecules and material synthesis. However, the reactions are usually sluggish and normally require acidic conditions with large excess of substrates to facilitate conversion, which limit their wide applications. Recent studies have shown that aniline as a nucleophilic catalyst can significantly accelerate the oxime/hydrazone formation reaction, preliminarily solving the reaction rate issue under mild and bio-compatible conditions. Therefore, it has been the most common coupling method in the modification of biological macromolecules. In this review, the design and development of aromatic amine catalyst in recent years as well as the catalytic mechanism and structure activity relationship are summarized. The application of highly active aniline catalysis in bioconjugations and material synthesis was also included together with a prospect for future development.
Key words： oxime; hydrazone; aniline catalysis; bioconjugation; material synthesis
Cai Mao , Han Yanfang , Zhang Qi , Luo Sanzhong . Aniline Catalysis in Bioconjugations and Material Synthesis[J]. Chinese Journal of Organic Chemistry, 2018 , 38(1) : 1 -10 . DOI: 10.6023/cjoc201708050
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