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An Unprecedented Effective Enzymatic Carboxylation of Phenols

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National Engineering Laboratory for Industrial Enzymes and Tianjin Engineering Research Center for Biocatalytic Technology Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, 32 Xi Qi Dao, Tianjin Airport Economic Area, Tianjin 300308, China
*E-mail for D.Z.: [email protected]. Fax: +86 22 84861996.
Cite this: ACS Catal. 2016, 6, 2, 564-567
Publication Date (Web):December 17, 2015
https://doi.org/10.1021/acscatal.5b02529
Copyright © 2015 American Chemical Society
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Abstract

Abstract Image

It is well-known that the equilibrium of the enzymatic Kolbe–Schmitt reaction is unfavorable for the carboxylation direction. A new method was developed to push the reaction equilibrium toward the carboxylation of resorcinol and catechol by adding quaternary ammonium salts into the reaction system. The yields of the carboxylation products were increased up to 97% from less than 40%. The precipitation capacity of the quaternary ammonium salts of the carboxylic acid products is the driving force for the reaction equilibrium shift. Therefore, effective enzymatic carboxylation of phenols has been achieved for the first time.

Cited By


This article is cited by 15 publications.

  1. Lars-Erik Meyer, Katharina Plasch, Udo Kragl, Jan von Langermann. Adsorbent-Based Downstream-Processing of the Decarboxylase-Based Synthesis of 2,6-Dihydroxy-4-methylbenzoic Acid. Organic Process Research & Development 2018, 22 (8) , 963-970. DOI: 10.1021/acs.oprd.8b00104.
  2. Xiang Sheng, Yury Patskovsky, Anna Vladimirova, Jeffrey B. Bonanno, Steven C. Almo, Fahmi Himo, Frank M. Raushel. Mechanism and Structure of γ-Resorcylate Decarboxylase. Biochemistry 2018, 57 (22) , 3167-3175. DOI: 10.1021/acs.biochem.7b01213.
  3. Chen Kaixun, Fan Yan, Cao Xupeng, Liu Jian, Tian Hao, Tian Jing. a novel green enzymatic synthetic route of 2, 3-dihydroxybenzoic acid from glucose and CO2 fixation. Process Biochemistry 2020, DOI: 10.1016/j.procbio.2020.04.030.
  4. Daniel Ohde, Benjamin Thomas, Simon Matthes, Zeynep Percin, Claudia Engelmann, Paul Bubenheim, Koichi Terasaka, Michael Schlüter, Andreas Liese. Fine Bubble‐based CO 2 Capture Mediated by Triethanolamine Coupled to Whole Cell Biotransformation. Chemie Ingenieur Technik 2019, 91 (12) , 1822-1826. DOI: 10.1002/cite.201900113.
  5. Mingzhu Ding, Biqiang Chen, Xiaojun Ji, Jingwen Zhou, Huiyuan Wang, Xiwei Tian, Xudong Feng, Hua Yue, Yongjin Zhou, Hailong Wang, Jianping Wu, Pengpeng Yang, Yu Jiang, Xuming Mao, Gang Xiao, Cheng Zhong, Wenhai Xiao, Bingzhi Li, Lei Qin, Jingsheng Cheng, Mingdong Yao, Ying Wang, Hong Liu, Lin Zhang, Linling Yu, Tao Chen, Xiaoyan Dong, Xiaoqiang Jia, Songping Zhang, Yanfeng Liu, Yong Chen, Kequan Chen, Jinglan Wu, Chenjie Zhu, Wei Zhuang, Sheng Xu, Pengfei Jiao, Lei Zhang, Hao Song, Sheng Yang, Yan Xiong, Yongquan Li, Youming Zhang, Yingping Zhuang, Haijia Su, Weiping Fu, Yingming Huang, Chun Li, Zongbao K. Zhao, Yan Sun, Guo-Qiang Chen, Xueming Zhao, He Huang, Yuguo Zheng, Lirong Yang, Zhiguo Su, Guanghui Ma, Hanjie Ying, Jian Chen, Tianwei Tan, Yingjin Yuan. Biochemical engineering in China. Reviews in Chemical Engineering 2019, 35 (8) , 929-993. DOI: 10.1515/revce-2017-0035.
  6. Yuta Sadamitsu, Akira Okumura, Kodai Saito, Tohru Yamada. Kolbe–Schmitt type reaction under ambient conditions mediated by an organic base. Chemical Communications 2019, 55 (66) , 9837-9840. DOI: 10.1039/C9CC04550C.
  7. Stefan E. Payer, Kurt Faber, Silvia M. Glueck. Non‐Oxidative Enzymatic (De)Carboxylation of (Hetero)Aromatics and Acrylic Acid Derivatives. Advanced Synthesis & Catalysis 2019, 375 DOI: 10.1002/adsc.201900275.
  8. Dennis Hülsewede, Lars‐Erik Meyer, Jan von Langermann. Application of In Situ Product Crystallization and Related Techniques in Biocatalytic Processes. Chemistry – A European Journal 2019, 25 (19) , 4871-4884. DOI: 10.1002/chem.201804970.
  9. Junting Hong, Man Li, Jianning Zhang, Beiqi Sun, Fanyang Mo. C−H Bond Carboxylation with Carbon Dioxide. ChemSusChem 2019, 12 (1) , 6-39. DOI: 10.1002/cssc.201802012.
  10. Immacolata C. Tommasi. Carboxylation of Hydroxyaromatic Compounds with HCO3− by Enzyme Catalysis: Recent Advances Open the Perspective for Valorization of Lignin-Derived Aromatics. Catalysts 2019, 9 (1) , 37. DOI: 10.3390/catal9010037.
  11. Chang Peng, Yuxue Liu, Xiaojia Guo, Wujun Liu, Qing Li, Zongbao K. Zhao. Selective carboxylation of substituted phenols with engineered Escherichia coli whole-cells. Tetrahedron Letters 2018, 59 (42) , 3810-3815. DOI: 10.1016/j.tetlet.2018.09.019.
  12. Xuemei Zhang, Jie Ren, Peiyuan Yao, Rui Gong, Min Wang, Qiaqing Wu, Dunming Zhu. Biochemical characterization and substrate profiling of a reversible 2,3-dihydroxybenzoic acid decarboxylase for biocatalytic Kolbe-Schmitt reaction. Enzyme and Microbial Technology 2018, 113, 37-43. DOI: 10.1016/j.enzmictec.2018.02.008.
  13. Jiang Duan, Wenhai Wu, Zengfeng Wei, Dedou Zhu, Haiyang Tu, Aidong Zhang. Synthesis of functional catechols as monomers of mussel-inspired biomimetic polymers. Green Chemistry 2018, 20 (4) , 912-920. DOI: 10.1039/C7GC03323K.
  14. Lorenzo Pesci, Pavel Gurikov, Andreas Liese, Selin Kara. Amine-Mediated Enzymatic Carboxylation of Phenols Using CO 2 as Substrate Increases Equilibrium Conversions and Reaction Rates. Biotechnology Journal 2017, 12 (12) , 1700332. DOI: 10.1002/biot.201700332.
  15. Xiao-Feng Wu, Feng Zheng. Synthesis of Carboxylic Acids and Esters from CO2. Topics in Current Chemistry 2017, 375 (1) DOI: 10.1007/s41061-016-0091-6.

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