Enhancement of Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquid with DMSO Co-solvent

doi:10.1016/j.cjche.2014.09.024

›› 2014, Vol. 22 ›› Issue (11/12): 1314-1321.DOI: 10.1016/j.cjche.2014.09.024

• BIOTECHNOLOGY AND BIOENGINEERING • Previous Articles Next Articles

Enhancement of Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquid with DMSO Co-solvent

Shuangshuang Gu, Jun Wang, Xianbin Wei, Hongsheng Cui, Xiangyang Wu, Fuan Wu

1 College of Biotechnology, Jiangsu University of Science and Technology, Zhenjiang 212018, China;
2 School of Environment and Safety Engineering, Jiangsu University, Zhenjiang 212013, China;
3 Sericultural Research Institute, Chinese Academy of Agricultural Sciences, Zhenjiang 212018, China

Received:2014-02-24 Revised:2014-04-22 Online:2014-12-24 Published:2014-12-28
Supported by:
Supported by the National Natural Science Foundation of China (21206061), the China Postdoctoral Science Foundation funded project (2012M510124, 2013T60505), the Natural Science Foundation of Jiangsu Province (BK2009213), the Qing Lan Project of Jiangsu Province (2014), the Graduate Innovation Project of Jiangsu Province (CXZZ13_0713), the Graduate Innovation Project of Jiangsu University of Science and Technology (2013), and the Postdoctoral Science Foundation funded project of Jiangsu University (1143002085).

Enhancement of Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquid with DMSO Co-solvent

1 College of Biotechnology, Jiangsu University of Science and Technology, Zhenjiang 212018, China;
2 School of Environment and Safety Engineering, Jiangsu University, Zhenjiang 212013, China;
3 Sericultural Research Institute, Chinese Academy of Agricultural Sciences, Zhenjiang 212018, China

通讯作者: Jun Wang, Xiangyang Wu
基金资助:
Supported by the National Natural Science Foundation of China (21206061), the China Postdoctoral Science Foundation funded project (2012M510124, 2013T60505), the Natural Science Foundation of Jiangsu Province (BK2009213), the Qing Lan Project of Jiangsu Province (2014), the Graduate Innovation Project of Jiangsu Province (CXZZ13_0713), the Graduate Innovation Project of Jiangsu University of Science and Technology (2013), and the Postdoctoral Science Foundation funded project of Jiangsu University (1143002085).

Abstract

Abstract: Caffeic acid phenethyl ester (CAPE) is a natural and rare ingredientwith several biological activities, but its industrial production using lipase-catalyzed esterification of caffeic acid (CA) and 2-phenylethanol (PE) in ionic liquids (ILs) is hindered by low substrate concentrations and long reaction time. To set up a high-efficiency bioprocess for production of CAPE, a novel dimethyl sulfoxide (DMSO)-IL co-solvent system was established in this study. The 2% (by volume) DMSO-[Bmim][Tf₂N] system was found to be the best medium with higher substrate solubility and conversion of CA. Under the optimum conditions, the substrate concentration of CA was raised 8-fold, the reaction timewas reduced by half, and the conversion reached 96.23%. The kinetics follows a ping-pong bi-bi mechanismwith inhibition by PE, with kinetic parameters as follows: V_max=0.89mmol · min^-1·g^-1, K_m,CA= 42.9mmol·L^-1, K_m,PE= 165.7mmol·L^-1, and K_i,PE= 146.2mmol·L^-1. The results suggest that the DMSO cosolvent effect has great potential to enhance the enzymatic synthesis efficiency of CAPE in ILs.

Key words: Biocatalysis, Caffeic acid phenethyl ester, Co-solvent, Kinetics, Ionic liquid

摘要： Caffeic acid phenethyl ester (CAPE) is a natural and rare ingredientwith several biological activities, but its industrial production using lipase-catalyzed esterification of caffeic acid (CA) and 2-phenylethanol (PE) in ionic liquids (ILs) is hindered by low substrate concentrations and long reaction time. To set up a high-efficiency bioprocess for production of CAPE, a novel dimethyl sulfoxide (DMSO)-IL co-solvent system was established in this study. The 2% (by volume) DMSO-[Bmim][Tf₂N] system was found to be the best medium with higher substrate solubility and conversion of CA. Under the optimum conditions, the substrate concentration of CA was raised 8-fold, the reaction timewas reduced by half, and the conversion reached 96.23%. The kinetics follows a ping-pong bi-bi mechanismwith inhibition by PE, with kinetic parameters as follows: V_max=0.89mmol · min^-1·g^-1, K_m,CA= 42.9mmol·L^-1, K_m,PE= 165.7mmol·L^-1, and K_i,PE= 146.2mmol·L^-1. The results suggest that the DMSO cosolvent effect has great potential to enhance the enzymatic synthesis efficiency of CAPE in ILs.

关键词: Biocatalysis, Caffeic acid phenethyl ester, Co-solvent, Kinetics, Ionic liquid

Shuangshuang Gu, Jun Wang, Xianbin Wei, Hongsheng Cui, Xiangyang Wu, Fuan Wu. Enhancement of Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquid with DMSO Co-solvent[J]. , 2014, 22(11/12): 1314-1321.

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Enhancement of Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquid with DMSO Co-solvent

Enhancement of Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquid with DMSO Co-solvent

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