Biotechnology Bulletin ›› 2023, Vol. 39 ›› Issue (9): 97-104.doi: 10.13560/j.cnki.biotech.bull.1985.2023-0028
Previous Articles Next Articles
CHEN Jin-hang1(), ZHANG Yi2, ZHANG Jun-tao1, WEI Ben-mei1, WANG Hong-xun1(), ZHENG Ming-ming1,2,3()
Received:
2023-01-13
Online:
2023-09-26
Published:
2023-10-24
Contact:
WANG Hong-xun, ZHENG Ming-ming
E-mail:chenjinhang2022@163.com;wanghongxunhust@163.com;zhengmingming@caas.cn
CHEN Jin-hang, ZHANG Yi, ZHANG Jun-tao, WEI Ben-mei, WANG Hong-xun, ZHENG Ming-ming. Preparation of Immobilized Lipase for the Solvent-free Synthesis of Cinnamyl Acetate[J]. Biotechnology Bulletin, 2023, 39(9): 97-104.
Fig. 2 Microscopic observation results of material OMS a: SEM results. b: TEM results. c: N2 adsorption-desorption of OMS, OMS-C8 and CSL@OMS-C8. d: Pore size distribution curves of OMS, OMS-C8 and CSL@OMS-C8
Fig. 5 Effects of different reaction conditions on the synthesis of cinnamyl acetate and comparison of immobilized and free enzymes under optimal conditions a: Effects of substrate molar ratio on the synthesis of cinnamyl acetate; b: effects of temperature on the synthesis of cinnamyl acetate; c: effects of enzyme loading on the synthesis of cinnamyl acetate; d: comparison of free enzyme and immobilized lipase under the optimal conditions
[1] | 中华人民共和国卫生部. 食品安全国家标准食品添加剂乙酸肉桂酯: GB 28345—2012[S]. 北京: 中国标准出版社, 2012. |
Ministry of Health of the People's Republic of China. Food additives. Cinnamyl acetate: GB 28345—2012[S]. Beijing: Standards Press of China, 2012. | |
[2] | 王召贺, 张云, 孙爱君, 等. 一种深海微生物脂肪酶在非水介质中催化合成乙酸肉桂酯的应用研究[J]. 食品工业科技, 2016, 37(9): 202-206. |
Wang ZH, Zhang Y, Sun AJ, et al. Synthesis of cinnamyl acetate by lipase- catalyzed trans- esterification[J]. Sci Technol Food Ind, 2016, 37(9): 202-206. | |
[3] |
Devulapelli VG, Weng HS. Synthesis of cinnamyl acetate by solid-liquid phase transfer catalysis: Kinetic study with a batch reactor[J]. Catal Commun, 2009, 10(13): 1638-1642.
doi: 10.1016/j.catcom.2009.04.032 URL |
[4] | 姚侠, 郑建永, 应向贤, 等. 有机相脂肪酶催化合成乙酸肉桂酯[J]. 生物加工过程, 2012, 10(3): 12-16. |
Yao X, Zheng JY, Ying XX, et al. Lipase-catalyzed synthesis of cinnamyl acetate in organic solvents[J]. Chin J Bioprocess Eng, 2012, 10(3): 12-16. | |
[5] | 黄文倩, 王迎夏, 田维圣, 等. 多酶催化级联反应在天然产物酶法合成中的应用研究进展[J]. 中国中药杂志, 2023, 48(2): 336-348. |
Huang WQ, Wang YX, Tian WS, et al. Research progress on application of multi-enzyme-catalyzed cascade reactions in enzymatic synthesis of natural products[J]. China J Chin Mater Med, 2023, 48(2): 336-348. | |
[6] | 陈曦, 吴凤礼, 樊飞宇, 等. 手性医药化学品的绿色生物合成[J]. 生物工程学报, 2022, 38(11): 4240-4262. |
Chen X, Wu FL, Fan FY, et al. Green biosynthesis of chiral pharmaceutical chemicals[J]. Chin J Biotechnol, 2022, 38(11): 4240-4262. | |
[7] |
Perdomo IC, Gianolio S, Pinto A, et al. Efficient enzymatic preparation of flavor esters in water[J]. J Agric Food Chem, 2019, 67(23): 6517-6522.
doi: 10.1021/acs.jafc.9b01790 URL |
[8] |
Berger RG. Biotechnology of flavours—the next generation[J]. Biotechnol Lett, 2009, 31(11): 1651-1659.
doi: 10.1007/s10529-009-0083-5 pmid: 19609491 |
[9] | 冉帆凡, 李露. SBA-15固定化酶的研究进展[J]. 食品研究与开发, 2022, 43(20): 206-212. |
Ran FF, Li L. Immobilized enzyme on SBA-15[J]. Food Res Dev, 2022, 43(20): 206-212. | |
[10] | 张璟譞, 高兵兵, 何冰芳. 生物催化中的酶固定化研究进展[J]. 生物加工过程, 2022, 20(1): 9-19, 40. |
Zhang JX, Gao BB, He BF. Research progress of enzyme immobilized in biocatalysis[J]. Chin J Bioprocess Eng, 2022, 20(1): 9-19, 40. | |
[11] |
Junior QCQ, Ferrarezi AL, Borges JP, et al. Hydrophobic adsorption in ionic medium improves the catalytic properties of lipases applied in the triacylglycerol hydrolysis by synergism[J]. Bioprocess Biosyst Eng, 2016, 39(12): 1933-1943.
doi: 10.1007/s00449-016-1667-9 URL |
[12] |
Pashangeh K, Akhond M, Karbalaei-heidari HR, et al. Biochemical characterization and stability assessment of Rhizopus oryzae lipase covalently immobilized on amino-functionalized magnetic nanoparticles[J]. Int J Biol Macromol, 2017, 105: 300-307.
doi: S0141-8130(17)30924-8 pmid: 28711611 |
[13] | 刘昱杉, 胡兴超, 丛方地, 等. 荧光假单胞菌脂肪酶(PFL)的固定化及催化合成乙酸肉桂酯[J]. 中国食品添加剂, 2015(6): 140-144. |
Liu YS, Hu XC, Cong FD, et al. Immobilization of Pseudomonas fluorescens lipase(PFL)and its catalysis in synthesis of cinnamyl acetate[J]. China Food Addit, 2015(6): 140-144. | |
[14] |
周美娟, 张莹, 丛方地, 等. 乙酸肉桂酯在固定化脂肪酶反应器中的合成[J]. 天津农学院学报, 2018, 25(1): 64-67, 80.
doi: 10.19640/j.cnki.jtau.2018.01.014 |
Zhou MJ, Zhang Y, Cong FD, et al. Synthesis of cinnamyl acetate in an immobilized-lipase bioreactor[J]. J Tianjin Agric Univ, 2018, 25(1): 64-67, 80. | |
[15] | 焦志勇. 酶在有序介孔材料上的固定化[J]. 中国石油和化工, 2016(S1): 84. |
Jiao ZY. Immobilization of enzyme on ordered mesoporous materials[J]. China Petroleum Chem Ind, 2016(S1): 84. | |
[16] |
Zheng MM, Zhu JX, Huang FH, et al. Enzymatic deacidification of the rice bran oil and simultaneous preparation of phytosterol esters-enriched functional oil catalyzed by immobilized lipase arrays[J]. Rsc Adv, 2015, 5(86): 70073-70079.
doi: 10.1039/C5RA11533G URL |
[17] |
Li YL, Zhang Y, Zhou YB, et al. A novel and controllable method for simultaneous preparation of human milk fat substitutes(OPL, OPO and LPL): two-step enzymatic ethanolysis-esterification strategy[J]. Food Res Int, 2023, 163: 112168.
doi: 10.1016/j.foodres.2022.112168 URL |
[18] | 王升帆, 王庭, 郗锋剑, 等. 固定化脂肪酶催化制备甘油三酯型鱼油[J]. 中国油脂, 2021, 46(8): 97-100, 109. |
Wang SF, Wang T, Xi FJ, et al. Preparation of triglyceride fish oil catalyzed by immobilized lipase[J]. China Oils Fats, 2021, 46(8): 97-100, 109. | |
[19] | 王舒舒, 张议丹, 石宏刚, 等. 响应面优化褶皱假丝酵母脂肪酶催化合成木质甾醇油酸酯[J]. 精细化工, 2021, 38(10): 2089-2095. |
Wang SS, Zhang YD, Shi HG, et al. Optimization of Candida rugosa lipase-catalyzed synthesis of lignosterol oleate by response surface methodology[J]. Fine Chem, 2021, 38(10): 2089-2095. | |
[20] |
Choi Y, Park JY, Chang PS. Integral stereoselectivity of lipase based on the chromatographic resolution of enantiomeric/regioisomeric diacylglycerols[J]. J Agric Food Chem, 2021, 69(1): 325-331.
doi: 10.1021/acs.jafc.0c07430 URL |
[21] |
Ma GC, Yan XQ, Li YL, et al. Ordered nanoporous silica with periodic 30-60 nm pores as an effective support for gold nanoparticle catalysts with enhanced lifetime[J]. J Am Chem Soc, 2010, 132(28): 9596-9597.
doi: 10.1021/ja1027524 pmid: 20578746 |
[22] |
Das SK, Bhunia MK, Sinha AK, et al. Synthesis, characterization, and biofuel application of mesoporous zirconium oxophosphates[J]. ACS Catal, 2011, 1(5): 493-501.
doi: 10.1021/cs200005z URL |
[23] |
Chen JH, Zhang Y, Zhong HY, et al. Efficient and sustainable preparation of cinnamic acid flavor esters by immobilized lipase microarray[J]. LWT, 2023, 173: 114322.
doi: 10.1016/j.lwt.2022.114322 URL |
[24] |
Xu LJ, Zhang Y, Zivkovic V, et al. Deacidification of high-acid rice bran oil by the tandem continuous-flow enzymatic reactors[J]. Food Chem, 2022, 393: 133440.
doi: 10.1016/j.foodchem.2022.133440 URL |
[25] |
朱彩林, 吕祥, 夏小乐. 盖子区域氨基酸的定点突变对T1脂肪酶酶学性质的影响[J]. 生物技术通报, 2020, 36(11): 94-102.
doi: 10.13560/j.cnki.biotech.bull.1985.2020-0220 |
Zhu CL, Lü X, Xia XL. Effect of site-directed mutagenesis of amino acids in lid region on the enzymatic properties of T1 lipase[J]. Biotechnol Bull, 2020, 36(11): 94-102. | |
[26] |
Wang Y, Zhang DH, Zhang JY, et al. High-yield synthesis of bioactive ethyl cinnamate by enzymatic esterification of cinnamic acid[J]. Food Chem, 2016, 190: 629-633.
doi: S0308-8146(15)00895-X pmid: 26213020 |
[27] |
Tomke PD, Rathod VK. Ultrasound assisted lipase catalyzed synthesis of cinnamyl acetate via transesterification reaction in a solvent free medium[J]. Ultrason Sonochemistry, 2015, 27: 241-246.
doi: 10.1016/j.ultsonch.2015.04.022 URL |
[28] |
Cai XH, Wang W, Lin L, et al. Cinnamyl esters synthesis by lipase-catalyzed transesterification in a non-aqueous system[J]. Catal Lett, 2017, 147(4): 946-952.
doi: 10.1007/s10562-017-1994-8 URL |
[29] |
Rodrigues RC, Virgen-Ortíz JJ, dos Santos JCS, et al. Immobilization of lipases on hydrophobic supports: immobilization mechanism, advantages, problems, and solutions[J]. Biotechnol Adv, 2019, 37(5): 746-770.
doi: S0734-9750(19)30062-X pmid: 30974154 |
[30] |
Bansode SR, Rathod VK. An investigation of lipase catalysed sonochemical synthesis: A review[J]. Ultrason Sonochemistry, 2017, 38: 503-529.
doi: 10.1016/j.ultsonch.2017.02.028 URL |
[31] |
Nieto S, Villa R, Donaire A, et al. Ultrasound-assisted enzymatic synthesis of xylitol fatty acid esters in solvent-free conditions[J]. Ultrason Sonochemistry, 2021, 75: 105606.
doi: 10.1016/j.ultsonch.2021.105606 URL |
[32] |
Zhang Y, Ng YL, Goh KL, et al. Fluidization of fungal pellets in a 3D-printed micro-fluidized bed[J]. Chem Eng Sci, 2021, 236: 116466.
doi: 10.1016/j.ces.2021.116466 URL |
[1] | WEI Xue, SUN Li-chao, LI Shu-ying, WANG Feng-zhong, XIN Feng-jiao. Immobilization of Lipase and Its Application in Food Industry [J]. Biotechnology Bulletin, 2016, 32(11): 59-64. |
[2] | Feng Shiyuan, Sun Tongwei, Mou Huiyan, Zhang Huitu, Lu Fuping. A Study on Transesterification and Acid-resistant Antiprotease of Carboxypeptidase in Porcine Pancreas [J]. Biotechnology Bulletin, 2015, 31(8): 193-199. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||