The Stereoselectivity of the Amidation Catalyzed by Lipase

Abstract

Abstract: An empirical rule for amidation of amines which contains chiral carbon catalyzed by lipase from candida antrarctica has been proposed, anDIt is the same one as alcohols. It can be used to predict that which enantiomer reacts faster based on the relative sizes of the substituents at the stereocenter, but the recognization is very delicate to the structure of the carbon contacted with amino group. The R-enantiomer reacts faster when the amines are secondary amines; the Senantiomer reacts faster when they are primary amines.

Key words: Lipase from Candida Antrarctica(CAL), Chiral carbong, Amidation, Enantioselectivity

CLC Number:

Q503

TrendMD:

YANG Bo, IZUMI Taeko, ZHANG Shu-Sheng . The Stereoselectivity of the Amidation Catalyzed by Lipase[J]. Chem. J. Chinese Universities, 2001, 22(8): 1332.

[1]	SHI Ge, XU Qian, DAI Xiao, ZHANG Jie, SHEN Jun, WAN Xinhua. Effect of Aromatic Substituent on Chiral Recognition of Helical Polyacetylene-based Chiral Stationary Phases for High-Performance Liquid Chromatography [J]. Chem. J. Chinese Universities, 2021, 42(8): 2673.
[2]	CHENG Xueli, LI Yanfei, ZHAO Yanyun, LIU Yongjun. Reaction Mechanism of Rh(I)-catalyzed Olefin Carboacylation:Enantioselectivity in the Formation of Chiral Poly-fused Rings^† [J]. Chem. J. Chinese Universities, 2018, 39(3): 521.
[3]	ZHOU Yamei, KONG Xiangzheng, HAN Hui, JIANG Xubao, ZHU Xiaoli. Easy Synthesis of Porous Polyurea and Its Application in Enzyme Immobilization and Kinetic Resolution of Racemic Phenylethanol^† [J]. Chem. J. Chinese Universities, 2017, 38(3): 495.
[4]	JIANG Haiyang, FENG Wei, SUN Yanwei, QI Qiaofang, TIAN Hongwei, LIU Huiling, HUANG Xuri. Theoretical Studies on the Conjugate Addition of 1-Bromonitromethane to Benzylidene Acetone Catalyzed by 9-Amino-9-deoxyepiquinine^† [J]. Chem. J. Chinese Universities, 2014, 35(7): 1500.
[5]	LI Chengyong, TAN Rong, ZHAO Jiangfeng, YIN Donghong. Ionic Liquid-functionalized Chiral salen Mn(Ⅲ) Complex for Asymmetric Oxidative Kinetic Resolution of Racemic Secondary Alcohols^† [J]. Chem. J. Chinese Universities, 2014, 35(2): 297.
[6]	TIAN Ye, WANG Ying-Jun, ZHOU Chang-Ren*, ZENG Qing-Hui, TAN Guo-Xing. Adhesion and Proliferation of Osteoblast on the Amidation Surface of Polylactide Film [J]. Chem. J. Chinese Universities, 2009, 30(12): 2491.
[7]	SHI Hong-Xin, LIN Hui, R. Bloch, G. Mandville . Enantioselective Synthesis of MK-287 [J]. Chem. J. Chinese Universities, 2004, 25(5): 874.
[8]	CHEN Xiao-Chuan, REN Xin-Feng, PENG Kun, WU Tong-Xing, PAN Xin-Fu . Enantioselective Synthesis of a Natural 8-O-4′ Neolignan Compound [J]. Chem. J. Chinese Universities, 2004, 25(1): 82.
[9]	GUO Zhao-Xia, LI Ying, YU Jian . Grafting of Dendritic Polyesters onto Nanometer Silica [J]. Chem. J. Chinese Universities, 2003, 24(6): 1139.
[10]	SHI Hong-Xin, LIN Hui, Bloch R., Mandville G., LIU Hua-Zhang. Synthesis of(2S,3S,4R)-2-n-Pentyl-3,4-diazidyl Tetrahydrothiofene [J]. Chem. J. Chinese Universities, 2002, 23(8): 1520.
[11]	SUN Cheng-Ke, YANG Si-Ya, MA Si-Yu, LI Zong-He . Theoretical Studies on Asymmetric Boron-catalyzed Reaction(Ⅰ) The Enantioselectivity in Oxazaborolidine-catalyzed Reductions of Phenyl Ethyl Ketone [J]. Chem. J. Chinese Universities, 2002, 23(1): 109.
[12]	ZHANG Zhi-Chao, ZHANG Kai, JIANG Zheng-Jin, ZHOU Qi-lin, WANG Qin-Sunt, GAO Ru-Yu. Enantioseparation of Chiral Drugs by Cyclodextrin-Mediated Capillary Zone Electrophoresis [J]. Chem. J. Chinese Universities, 2001, 22(S1): 42.
[13]	GU Wen-Xin, WU Tong-Xing, CHEN Xiao-Chuan, PAN Xin-Fu . First Enantioselective Syntheses of (2R,3R)- and (2S,3S)-3-(4-Hydroxy-3- methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde [J]. Chem. J. Chinese Universities, 2001, 22(1): 70.
[14]	LI Ting-You, WANG Li-Ping, ZHANG Tao, LI Yao-Xian, WANG Zong-Mu. Studies on the Stereoselectivity of Pinacol Coupling Reaction Mediated by TiCl₄-Mg [J]. Chem. J. Chinese Universities, 2000, 21(9): 1391.
[15]	CHEN Hui, LU Xian-Yu, HUANG Jun-Min, GAO Ru-Yu, WANG Qin-Sun . Investigation of Retention and Chiral Recognition Mechanism of the Derivative β-Cyclodextrin Bonded Stationary Phase [J]. Chem. J. Chinese Universities, 2000, 21(4): 562.

The Stereoselectivity of the Amidation Catalyzed by Lipase

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments