Chemoenzymatic Relay Reaction and Its Applications in Highly Efficient and Green Synthesis of High-Value Chiral Compounds
- Corresponding author: Xiong Xingquan, xxqluli@hqu.edu.cn
Citation:
Liao Xu, Jiang Yan, Lai Shilin, Liu Yuangang, Wang Shibin, Xiong Xingquan. Chemoenzymatic Relay Reaction and Its Applications in Highly Efficient and Green Synthesis of High-Value Chiral Compounds[J]. Chinese Journal of Organic Chemistry,
;2019, 39(3): 668-678.
doi:
10.6023/cjoc201807038
Katja, G.; Kirsten, S.; Stephan, L.; Andreas, L. Appl. Microbiol. Biotechnol. 2007, 76, 24.
Ni, Y.; Li, C. C.; Ma, H. M.; Zhang, J.; Xu, J. H. Appl. Mierobiol. Biotechnol. 2010, 89, 1111.
Patel, R. N. Coord. Chem. Rev. 2008, 252, 659.
doi: 10.1016/j.ccr.2007.10.031
Wang, H.; Zong, M. H.; Wu, H. J. Biotechnology 2007, 129, 689.
Makkee, M.; Kieboom, A. P. G.; van Bekkum, H. J. Chem. Soc., Chem. Commun. 1980, 930.
Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859.
doi: 10.1016/0040-4039(96)00136-0
Dinh, P. M.; Howarth, J. A.; Hudnott, A. R.; Williams, J. M. J.; Harris, W. Tetrahedron Lett. 1996, 37, 7623.
doi: 10.1016/0040-4039(96)01677-2
Carr, R.; Alexeeva, M.; Dawson, M. J.; Fernandez, V. G.; Humphrey, C. E.; Turner, N. J. ChemBioChem 2005, 6, 637.
doi: 10.1002/cbic.v6:4
Bisogno, F. R.; Lopez-Vidal, M. G.; de Gonzalob, G. Adv. Synth. Catal. 2017, 359, 2026.
doi: 10.1002/adsc.v359.12
Schrittwieser, J. H.; Velikogne, S.; Hall, M.; Kroutil, W. Chem. Rev. 2018, 118, 270.
doi: 10.1021/acs.chemrev.7b00033
Rudroff, F.; Mihovilovic, A. D.; Gröger, H.; Radka, S.; Hans, I.; Uwe, T. B. Nat. Catal. 2018, 1, 12.
doi: 10.1038/s41929-017-0010-4
Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859.
doi: 10.1016/0040-4039(96)00136-0
Pamies, O.; Backvall, J. E. Chem. Rev. 2003, 103, 3247.
doi: 10.1021/cr020029g
Burda, E.; Hummel, W.; Groger, H. Angew. Chem., Int. Ed. 2008, 47, 9551.
doi: 10.1002/anie.v47:49
Sato, H.; Hummel, W.; Groger, H. Angew. Chem., Int. Ed. 2015, 54, 4488.
doi: 10.1002/anie.201409590
Ahmed, S. T.; Parmeggiani, F.; Weise, N. J.; Flitsch, S. L.; Turner, N. J. ACS Catal. 2015, 5, 5410.
doi: 10.1021/acscatal.5b01132
Latham, J.; Henry, J, M.; Sharif, H, H.; Menon, B. R. K.; Shepherd, S. A.; Greaney, M. F.; Micklefield, J. Nat. Commun. 2016, 7, 11873.
doi: 10.1038/ncomms11873
Rodriguez-Alvarez, M. J.; Rios-Lombardia, N.; Schumacher, S.; Perez-Iglesias, D.; Moris, F.; Cadierno, V.; Garcia-Alvarez, J.; Gonzalez-Sabín, J. ACS Catal. 2017, 7, 7753.
doi: 10.1021/acscatal.7b02183
Denard, C. A.; Bartlett, M. J.; Wang, Y. J.; Lu, L.; Hartwig, J. F.; Zhao, H.-M. ACS Catal. 2015, 5, 3817.
doi: 10.1021/acscatal.5b00533
Denard, C. A.; Huang, H.; Bartlett, M. J.; Lu, L.; Tan, Y.; Zhao, H.-M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2014, 53, 465.
doi: 10.1002/anie.v53.2
Rios-Lombardia, N.; Vidal, C.; Cocina, M.; Moris, F.; Garcia-Alvarez, J.; Gonzalez-Sabin, J. Chem. Commun. 2015, 51, 10937.
doi: 10.1039/C5CC03298A
Sosa, V.; Melkie, M.; Sulca, C.; Li, J.; Tang, L.; Li, J.; Faris, J.; Foley, B.; Banh, T.; Kato, M.; Cheruzel, L. E. ACS Catal. 2018, 8, 2225.
doi: 10.1021/acscatal.7b04160
Haak, R. M.; Berthiol, F.; Jerphagnon, T.; Gayet, A. J. A.; Tarabiono, C.; Postema, C. P.; Ritleng, V.; Pfeffer, M.; Janssen, D. B.; Minnaard, A. J.; Feringa, B. L.; de Vries J. G. J. Am. Chem. Soc. 2008, 130, 135008.
Mutti, F. G.; Orthaber, A.; Schrittwieser, J. H.; de Vries, J. G.; Pietschnig, R.; Kroutil, W. Chem. Commun. 2010, 46, 8046.
doi: 10.1039/c0cc02813d
Wang, Z. J.; Clary, K. N.; Bergman, R. G.; Raymond, K. N.; Toste, F. D. Nat. Chem. 2013, 5, 100.
doi: 10.1038/nchem.1531
Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2006, 45, 745.
doi: 10.1002/(ISSN)1521-3773
Merlau, M. L.; Mejia, M. D. P.; Nguyen, S. T.; Hupp, J. T. Angew. Chem., Int. Ed. 2001, 40, 4239.
doi: 10.1002/1521-3773(20011119)40:22<>1.0.CO;2-D
Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. Angew. Chem., Int. Ed. 2007, 46, 2366.
doi: 10.1002/(ISSN)1521-3773
Schaaf, P.; Gojic, V.; Bayer, T.; Rudroff, F.; Schnurch, M.; Mihovilovic, M. ChemCatChem 2018, 10, 920.
doi: 10.1002/cctc.201701752
Cuetos, A.; Bisogno, F. R.; Lavandera, I.; Gotor, V. Chem. Commun. 2013, 49, 2625.
doi: 10.1039/c3cc38674k
Wang, J.-X.; Li, K.; Zhou, X.-J.; Han, W.-Y.; Wan, N.-W.; Cui, B.-D.; Wang, H.-H.; Yuan, W.-C.; Chen, Y.-Z. Tetrahedron Lett. 2017, 58, 2252.
doi: 10.1016/j.tetlet.2017.04.074
Baer, K.; Krauber, M.; Burda, E.; Hummel, W.; Berkessel, A.; Grçger, H. Angew. Chem., Int. Ed. 2009, 48, 9355.
doi: 10.1002/anie.v48:49
Rulli, G.; Dunangdee, N.; Baer, K.; Hummel, W.; Berkessel, A.; Grçger, H. Angew. Chem., Int. Ed. 2011, 50, 7944.
doi: 10.1002/anie.v50.34
Heidlindemann, M.; Rulli, G.; Berkessel, A.; Hummel, W.; Grçger, H. ACS Catal. 2014, 4, 1099.
doi: 10.1021/cs4010387
Simon, R. C.; Busto, E.; Schrittwiesser, J. H.; Sattler, J. H.; Pietruszka, S. J.; Faber, K.; Kroutil, W. Chem. Commun. 2014, 50, 15669.
doi: 10.1039/C4CC06230B
Akagawa, K.; Kudo, K. Adv. Synth. Catal. 2011, 353, 843.
doi: 10.1002/adsc.v353.6
Akagawa, K.; Fujiwara, T.; Sakamoto, S.; Kudo, K. Chem. Commun. 2010, 46, 8040.
doi: 10.1039/c0cc02301a
Akagawa, K.; Umezawa, R.; Kudo, K. Beilstein J. Org. Chem. 2012, 8, 1333.
doi: 10.3762/bjoc.8.152
Hafenstine, G. R.; Ma, K.; Harris, A. W.; Yehezkeli, O.; Park, E. Domaille, D. W.; Cha, J. N.; Goodwin, A. P. ACS Catal. 2017, 7, 568.
doi: 10.1021/acscatal.6b03213
Sujic, S.; Pietruszka, J.; Worgull, D. Adv. Synth. Catal. 2015, 357, 1822.
doi: 10.1002/adsc.201500183
Akagawa, K.; Kudo, K. Org. Lett. 2011, 13, 3498.
doi: 10.1021/ol2012956
Parmeggiani, F.; Ahmed, S. T.; Weise, N. J.; Turner, N. J. Tetrahedron 2016, 72, 7256.
doi: 10.1016/j.tet.2015.12.063
Ahmed, S. T.; Parmeggiani, F.; Weise, N. J.; Flitsch, S. L.; Turner, N. J. Org. Lett. 2016, 18, 5468.
doi: 10.1021/acs.orglett.6b02559
Xu, Y.-F.; Wang, M.; Feng, B.; Li, Z.-Y.; Li, Y.-H.; Li, H.-X.; Li, H. Catal. Sci. Technol. 2017, 7, 5838.
doi: 10.1039/C7CY01954H
Kotlewska, A. J.; Rantwijk, F. V.; Sheldon, R. A.; Arends, I. W. C. E. Green Chem. 2011, 13, 2154.
doi: 10.1039/c1gc15255f
Zhou, P.-F.; Wang, X.-P.; Yang, B.; Hollmannc, F.; Wang, Y.-H. RSC Adv. 2017, 7, 12518.
doi: 10.1039/C7RA00805H
Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
Liwei Wang , Guangran Ma , Li Wang , Fugang Xu . A Comprehensive Analytical Chemistry Experiment: Colorimetric Detection of Vitamin C Using Nanozyme and Smartphone. University Chemistry, 2024, 39(8): 255-262. doi: 10.3866/PKU.DXHX202312094
Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194
Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
.
CCS Chemistry 综述推荐│绿色氧化新思路:光/电催化助力有机物高效升级
. CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO2 reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022