Efficient synthesis of vitamin E intermediate by lipase-catalyzed regioselective transesterification

作者: Chun Wei , Xian-Feng Fu , Zhao Wang , Xin-Jun Yu , Yin-Jun Zhang

DOI: 10.1016/J.MOLCATB.2014.05.003

关键词: Substrate (chemistry)ButanolSolventTransesterificationAlcoholBiocatalysisLipaseCatalysisChemistryOrganic chemistry

摘要: Abstract Trimethylhydroquinone-1-monoacetate (TMHQ-1-MA) is a valuable synthetic intermediate for vitamin E acetate. Immobilized Lipozyme RM IM from Mucor miehei was shown to be the best biocatalyst production of TMHQ-1-MA through regioselective transesterification between trimethylhydroquinone diacetate (TMHQ-DA) and alcohol. The effects lipase-catalyzed reaction conditions including solvent, acyl receptor, substrate mole ratio, temperature agitation speed were investigated. optimum catalyzed achieved at ratio 1:1, an 200 rpm 50 °C in MTBE/ n -hexane (3:7). Under above conditions, exhibited high tolerance (substrate concentrations 1.06 M). Recycling experiments demonstrated that quite steady under conditions. analysis kinetic experiment showed enzymatic obeys Ping–Pong bi–bi mechanism with -butanol inhibition.

参考文章(22)
Regina Brigelius‐Flohé, Maret G. Traber, Vitamin E: function and metabolism The FASEB Journal. ,vol. 13, pp. 1145- 1155 ,(1999) , 10.1096/FASEBJ.13.10.1145
S. Bradoo, R. K. Saxena, R. Gupta, High Yields of Ascorbyl Palmitate by Thermostable Lipase-Mediated Esterification Journal of the American Oil Chemists' Society. ,vol. 76, pp. 1291- 1295 ,(1999) , 10.1007/S11746-999-0141-0
David J. Pollard, John M. Woodley, Biocatalysis for pharmaceutical intermediates: the future is now Trends in Biotechnology. ,vol. 25, pp. 66- 73 ,(2007) , 10.1016/J.TIBTECH.2006.12.005
Werner Bonrath, Manfred Eggersdorfer, Thomas Netscher, Catalysis in the industrial preparation of vitamins and nutraceuticals Catalysis Today. ,vol. 121, pp. 45- 57 ,(2007) , 10.1016/J.CATTOD.2006.11.021
Ganapati D. Yadav, Piyush S. Lathi, Kinetics and mechanism of synthesis of butyl isobutyrate over immobilised lipases Biochemical Engineering Journal. ,vol. 16, pp. 245- 252 ,(2003) , 10.1016/S1369-703X(03)00026-3
J. Jacoby, A. Pasc, C. Carteret, F. Dupire, M.J. Stébé, V. Coupard, J.L. Blin, Ordered mesoporous materials containing Mucor Miehei Lipase as biocatalyst for transesterification reaction Process Biochemistry. ,vol. 48, pp. 831- 837 ,(2013) , 10.1016/J.PROCBIO.2013.04.003
Linga Banoth, Manpreet Singh, Alemu Tekewe, Uttam Banerjee, Increased enantioselectivity of lipase in the transesterification of dl-(±)-3-phenyllactic acid in ionic liquids Biocatalysis and Biotransformation. ,vol. 27, pp. 263- 270 ,(2009) , 10.1080/10242420903049903
Ganapati D. Yadav, Indrakant V. Borkar, Kinetic and Mechanistic Investigation of Microwave-Assisted Lipase Catalyzed Synthesis of Citronellyl Acetate Industrial & Engineering Chemistry Research. ,vol. 48, pp. 7915- 7922 ,(2009) , 10.1021/IE800591C
Ganapati D. Yadav, Shrikant B. Dhoot, Immobilized lipase-catalysed synthesis of cinnamyl laurate in non-aqueous media Journal of Molecular Catalysis B-enzymatic. ,vol. 57, pp. 34- 39 ,(2009) , 10.1016/J.MOLCATB.2008.06.013
Daniel C. Liebler, The role of metabolism in the antioxidant function of vitamin E. Critical Reviews in Toxicology. ,vol. 23, pp. 147- 169 ,(1993) , 10.3109/10408449309117115