非水相体系中木瓜脂肪酶催化合成萜烯醇芳香酯的研究

doi:10.3969/j.issn.0253-2417.2015.01.007

Abstract

Abstract: In order to establish economic, green and efficient synthesis process of terpene alcohol aromatic ester, naturally immobilized Carica papaya lipase (CPL) was prepared from the crude papain, and was used to catalyze the synthesis of terpene alcohol aromatic ester in non-aqueous system. The effects of terpene alcohol type, organic solvent type, and initial water activity on the CPL catalyzed reaction were investigated. The results showed that the primary terpene alcohols (geraniol and citronellol) were more suitable substrates, solvents with moderate polarity such as n-hexane were suitable reaction medium, and initial water activity of 0.328 benefitted the catalytic activity of CPL in organic solvents. Under these conditions, the substrate conversion rate was 95.2%, which was similar to those of commercial lipases. The reusability of CPL in organic solvent was poor. Three treatment methods by introduction of the ionic liquid were investigated on their effects on CPL catalyzed performance. It was found that wrapping the CPL with trace amount of ionic liquid before use could significantly enhance the CPL stability. The catalytic activity of CPL still remained more than 90% after being used in the organic solvent for 15 batches.

Key words: non-aqueous system, Carica papaya lipase, terpene alcohol, aromatic ester

CLC Number:

TQ35
Q939.9

SU Er-zheng, YOU Peng-yong, WEI Dong-zhi. Catalytic Synthesis of Terpene Alcohol Aromatic Ester with Carica papaya Lipase in Non-aqueous System[J]. Chemistry and Industry of Forest Products, 2015, 35(1): 45-50.

References

[1] HOURIA A,LOUIS C.Aroma synthesis by immobilized lipase from Mucor sp[J].Enzyme and Microbial Technology,2003,32(5):589-595.
[2] GANAPATI D,YADAV A,TRIVEDI H.Kinetic modeling of immobilized-lipase catalyzed transesterification of n-octanol with vinyl acetate in non-aqueous media[J].Enzyme and Microbial Technology,2003,32(7):783-789.
[3] AKOH C C,YEE L N.Lipase-catalyzed transesterification of primary terpene alcohols with vinyl esters in organic media[J].Journal of Molecular Catalysis B:Enzymatic,1998,4(3):149-153.
[4] ATHAWALE V,MANJREKAR N,ATHAWALE M.Effect of reaction parameters on synthesis of citronellyl methacrylate by lipase-catalyzed transesterification[J].Biotechnology Progress,2003,19(2):298-302.
[5] HABULIN M,ŠABEDER S,SAMPEDRO M A,et al.Enzymatic synthesis of citronellol laurate in organic media and in supercritical carbon dioxide[J].Biochemical Engineering Journal,2008,42 (1):6-12.
[6] GRYGLEWICZ S,JADOWNICKA E,CZEMIAK A.Lipase catalysed synthesis of aliphatic,terpene and aromatic esters by alcoholysis in solvent-free medium[J].Biotechnology Letters,2000,22(17) :1379-1382.
[7] GANDHI N N,MUKHERJEE K D.Specificity of papaya lipase in esterification with respect to the chemical structure of substrates[J].Journal Agricultural Food Chemistry,2000,48(2):566-570.
[8] YANG L,DORDICK J S,GARDE S.Hydration of enzyme in nonaqueous media is consistent with solvent dependence of its activity[J].Biophysical Journal,2004,87(2):812-821.
[9] CHEN C C,TSAI S W.Carica papaya lipase:A novel biocatalyst for the enantioselective hydrolysis of (R,S)-naproxen 2,2,2-trifluoroethyl ester[J].Enzyme and Microbial Technology,2005,36 (1):127-132.
[10] BRIGITTE B,KURT F.Immunization of lipase against acetaldehyde emerging in acyl transfer reactions from vinyl acetate[J].Journal of the Chemical Society,Chemical Communications,1991,17 (1):1198-1200.
[11] 徐晓冬,李欣欣,丹媛媛,等.离子液体在生物催化反应中的应用[J].生物技术通报,2008(4):34-37. XU Xiao-dong,LI Xin-xin,DAN Yuan-yuan,et al.Application of ionic liquids in biocatalytic reactions[J].Biotechnology Bulletin,2008(4):34-37.
[12] 夏咏梅,吴红平,张玥,等.离子液体的制备及其在酶催化反应中的应用[J].化学进展,2006,18 (12):1660-1667. XIA Yong-mei,WU Hong-ping,ZHANG Yue,et al.Synthesis and application of Ionic liquids in enzymatic catalysis[J].Progress in Chemistry,2006,18(12):1660-1667.
[13] SUSHEEL J N,JITENDRA R H,MANIKRAO M S.Lipase-catalysed transesterification in ionic liquids and organic solvents:A comparative study[J].Tetrahedron Letters,2002,43 (16):2979-2982.
[14] TOSHIYUKI I,YUICHI M.Increased enantioselectivity and remarkable acceleration of lipase-catalyzed transesterification by using an imidazolium PEG-alkyl sulfate ionic liquid[J].Chemistry:A European Journal,2006,12 (36):9228 -9237.
[15] LEE J K,KIM M J.Ionic liquid-coated enzyme for biocatalysis in organic solvent[J].The Journal of Organic Chemistry,2002,67 (19):6845-6847.

Catalytic Synthesis of Terpene Alcohol Aromatic Ester with Carica papaya Lipase in Non-aqueous System

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	MA Shuai, HU Xiaoying, DONG Changqing, ZHAO Ying, WANG Xiaoqiang, ZHAO Jin. Research Progress in the Removal of Biomass Tar Model Compounds [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 1-8.
[2]	XING Jianxiong, ZHENG Kai, HAN Zunqiang, XU Weitao, WANG Kun. Research Progress on Application of Cellulose-based Materials as Electrode in Flexible Supercapacitor [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 9-17.
[3]	CHEN Jinwei, WANG Dan, SHANG Shibin, LIU He, CAI Zhaosheng. Preparation of Amino-terminated Hyperbranched Polymer Grafted Dialdehyde-based Nanocellulose and Its Adsorption Properties of Ni²⁺ [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 18-26.
[4]	WANG Xiaoyu, DUAN Wengui, LIN Guishan, KANG Guoqiang, SHANG Minghao, LEI Fuhou. Synthesis and Antifungal Activity of (Z)-/(E)-Verbenone Oxime Ether Compounds [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 27-34.
[5]	ZHANG Qingtong, YUN Xiaojing, YAN Depeng, LI Mingfu, WANG Shuangfei, MIN Douyong. Preparation of Sliver Nanoparticles by Lignin Under Solar Light Irradiation [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 35-41.
[6]	CHEN Jian, WU Guomin, HUO Shuping, KONG Zhenwu. Synthesis and Characterization of Allyl Cardanol Monomer with Ether Bond and Ester Bond [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 42-48.
[7]	CHEN Yan, WANG Zixin, LI Qizhen, XIA Jianyu, LIU Zhulan, CAO Yunfeng. Synthesis and Characterization of Lignocellulose Oil-absorbing Aerogels [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 49-55.
[8]	WU Shaoji, JIANG Kun, YE Yueyuan, LIU Yunquan, WANG Duo, LI Shuirong. Preparation of Activated Carbon from Co-pyrolysis Char of Sewage Sludge and Poplar Sawdust and Its Application in Wastewater Treatment [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 56-64.
[9]	WANG Pengfei, REN Hao, ZHAI Huamin. P-factor Regulation of Characteristics in the Auto Hydrolysis ofPoplar Carbohydrate [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 65-71.
[10]	XIONG Mingcheng, WANG Zi, YAN Yuxin, ZHENG Yanling, XIAO Zhenzhen, LU Qilin, HUANG Biao. Preparation of Nanocrystalline Cellulose by the Catalytic Hydrolysis of Pulp with p-Toluenesulfonic Acid Under Ultrasonication [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 72-76.
[11]	LIU Yijun, YUAN Yuan, LIU Yangyang, ZHANG Fan, LI Jihua. Effects of Different Drying Methods on Physicochemical Properties and Essential Oil Quality of Melaleuca alternifolia Cheel [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 77-82.
[12]	WANG Xiaojie, HUANG Lixin, ZHANG Caihong, XIE Pujun, DENG Yejun, LIU Lujie. Preparation and Physicochemical Properties of Olive Leaf Extract [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 83-90.
[13]	PENG Yan, TANG Kehua, DONG Aiwen. Purification of Bletilla striata Polyphenols by Macroporous Resin and Its Antioxidant Activities in Vitro [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 91-99.
[14]	LI Junjie, DONG Yun, ZHAO Huaping, MA Hongxia. Synthesis and Characterization of Cardanol-based Epoxy Resin Containing A Cyclotriphosphazene Core [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 100-104.
[15]	ZHOU Jing, GUI Yuhao, GONG Shengzhao. Antioxidant Activity of Tea Seed Shell Fermentation Extracts and Its Inhibitory Effect on Intracellular Oxidative Damage [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 105-112.