Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (1): 1-10.DOI: 10.6023/cjoc201708050 Previous Articles     Next Articles

Special Issue: 庆祝吴养洁院士九十华诞专辑



蔡茂a,b, 韩彦方a,b, 章琪a,b, 罗三中a,b   

  1. a 中国科学院化学研究所 分子识别与功能重点实验室 北京 100190;
    b 中国科学院大学 北京 100049
  • 收稿日期:2017-08-23 修回日期:2017-09-28 发布日期:2017-10-11
  • 通讯作者: 罗三中
  • 基金资助:


Aniline Catalysis in Bioconjugations and Material Synthesis

Cai Maoa,b, Han Yanfanga,b, Zhang Qia,b, Luo Sanzhonga,b   

  1. a Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190;
    b University of Chinese Academy of Sciences, Beijing 100049
  • Received:2017-08-23 Revised:2017-09-28 Published:2017-10-11
  • Contact: 10.6023/cjoc201708050
  • 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