Citation:
Fu Jianping, Han Xiaodan, Hu Juwu, Wang Huibin, Xiong Wei, Li Xionghui. Papain-Catalyzed Asymmetric Aldol Reactions of Heterocyclic Ketoneswith Aldehydes[J]. Chemistry,
;2016, 79(11): 1052-1057.
-
The new promiscuous activity of papain has been observed to catalyze the direct asymmetric Aldol reaction of heterocyclic ketones with aromatic aldehydes. We studied the effects of solvent, water content, ratio of substrates, enzyme loading and temperature on the reaction. Papain showed favorable catalytic activity and had a good adaptability to different substrates in the reaction. Up to 37% yield and 78% ee were achieved under optimal conditions. It is interesting that papain possesses the function of aldolase in organic solvents.
-
-
-
[1]
[1] 王晓光, 段青, 栾兴社. 化工科技, 2007,1:71~75.
-
[2]
[2] U T Bornscheuer, R J Kazlauskas. Angew. Chem. Int. Ed., 2004, 43(45):6032~6040.
-
[3]
[3] E Busto, V G Fernández, V Gotor. Chem. Soc. Rev., 2010, 39:4504~4523.
-
[4]
[4] W B Wu, N Wang, J M Xu et al. Chem. Commun., 2005, 18:2348~2350.
-
[5]
[5] F W Lou, B K Liu, Q Wu et al. Adv. Synth. Catal., 2008, 350(13):1959~1962.
-
[6]
[6] W B Wu, J M Xu, Q Wu et al. Adv. Synth. Catal., 2006, 348(4-5):487~492.
-
[7]
[7] R C Tang, Z Guan, Y H He et al. J. Mol. Catal. B:Enzym., 2010, 63(1-2):62~67.
-
[8]
[8] J L Wang, X Li, H Y Xie et al. J. Biotechnol., 2010,145(3):240~243.
-
[9]
[9] H Sasai, T Suzuki, N Itoh. Tetrahed. Lett., 1993, 34(5):851~854.
-
[10]
[10] A Abiko, J Liu, S Masamune. J. Am. Chem. Soc., 1997, 119(10):2586~2587.
-
[11]
[11] J R Chen, X Y Li, X N Xing et al. J. Org. Chem., 2006, 71(21):8198~8202.
-
[12]
[12] P M Pihko, K M Laurikainen, A Usano et al. Tetrahedron, 2006, 62(2-3):317~328.
-
[13]
[13] C Li, X W Feng, N Wang et al. Green Chem., 2008, 10:616~618.
-
[14]
[14] Z Guan, J P Fu, Y H He. Tetrahed. Lett., 2012, 53(37):4959~4961.
-
[1]
-
-
-
[1]
Yuting Zhang , Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037
-
[2]
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
-
[3]
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
-
[4]
Guilan He , Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122
-
[5]
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
-
[6]
Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
-
[7]
Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
-
[8]
Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
-
[9]
Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
-
[10]
Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
-
[11]
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
-
[12]
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
-
[13]
Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
-
[14]
Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
-
[15]
Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
-
[16]
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
-
[17]
Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
-
[18]
Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
-
[19]
Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
-
[20]
Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(280)
- HTML views(12)