An enantioselective artificial Suzukiase based on the biotin–streptavidin technology
作者： Anamitra Chatterjee , Hendrik Mallin , Juliane Klehr , Jaicy Vallapurackal , Aaron D. Finke
DOI: 10.1039/C5SC03116H
关键词:
摘要: Introduction of a biotinylated monophosphine palladium complex within streptavidin affords an enantioselective artificial Suzukiase. Site-directed mutagenesis allowed the optimization activity and enantioselectivity this metalloenzyme. A variety atropisomeric biaryls were produced in good yields up to 90% ee. The hybrid catalyst described herein shows comparable TOF previous aqueous-asymmetric Suzuki catalysts, excellent stability under reaction conditions realize higher TON through longer time.
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lib4ri.ch参考文章(41)
Maiyun Yang, Jie Li, Peng R. Chen, Transition metal-mediated bioorthogonal protein chemistry in living cells Chemical Society Reviews. ,vol. 43, pp. 6511- 6526 ,(2014) , 10.1039/C4CS00117F
Laure Benhamou, Céline Besnard, E. Peter Kündig, Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki–Miyaura Coupling Reactions Organometallics. ,vol. 33, pp. 260- 266 ,(2014) , 10.1021/OM4009982
Sambasivarao Kotha, Kakali Lahiri, Dhurke Kashinath, Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis Tetrahedron. ,vol. 58, pp. 9633- 9695 ,(2002) , 10.1016/S0040-4020(02)01188-2
Rahimi M. Yusop, Asier Unciti-Broceta, Emma M. V. Johansson, Rosario M. Sánchez-Martín, Mark Bradley, Palladium-mediated intracellular chemistry Nature Chemistry. ,vol. 3, pp. 239- 243 ,(2011) , 10.1038/NCHEM.981
Adam F. Littke, Gregory C. Fu, Palladium-Catalyzed Coupling Reactions of Aryl Chlorides Angewandte Chemie International Edition. ,vol. 41, pp. 4176- 4211 ,(2002) , 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
Xiaoqiang Shen, Gavin O. Jones, Donald A. Watson, Brijesh Bhayana, Stephen L. Buchwald, Enantioselective Synthesis of Axially Chiral Biaryls by the Pd-Catalyzed Suzuki-Miyaura Reaction: Substrate Scope and Quantum Mechanical Investigations Journal of the American Chemical Society. ,vol. 132, pp. 11278- 11287 ,(2010) , 10.1021/JA104297G
Norio. Miyaura, Akira. Suzuki, Palladium-catalyzed cross-coupling reactions of organoboron compounds Chemical Reviews. ,vol. 95, pp. 2457- 2483 ,(1995) , 10.1021/CR00039A007
Antonio Bermejo, Abel Ros, Rosario Fernández, José M. Lassaletta, C2-symmetric bis-hydrazones as ligands in the asymmetric Suzuki-Miyaura cross-coupling. Journal of the American Chemical Society. ,vol. 130, pp. 15798- 15799 ,(2008) , 10.1021/JA8074693
T. K. Hyster, L. Knorr, T. R. Ward, T. Rovis, Biotinylated Rh(III) Complexes in Engineered Streptavidin for Accelerated Asymmetric C–H Activation Science. ,vol. 338, pp. 500- 503 ,(2012) , 10.1126/SCIENCE.1226132
Jérôme Collot, Nicolas Humbert, Myriem Skander, Gérard Klein, Thomas R. Ward, Artificial metalloenzymes for enantioselective catalysis: the phenomenon of protein accelerated catalysis Journal of Organometallic Chemistry. ,vol. 689, pp. 4868- 4871 ,(2004) , 10.1016/J.JORGANCHEM.2004.09.032