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非水介质中微波辅助酶促动力学拆分（±）-1-苯基-2-丙炔-1-醇

Microwave assisted enzymatic kinetic resolution of (±)-1-phenyl-2-propyn-1-ol in nonaqueous media.

作者信息

Devendran Saravanan, Yadav Ganapati D

机构信息

Department of Chemical Engineering, Institute of Chemical Technology, Matunga, Mumbai 400 019, India.

出版信息

Biomed Res Int. 2014;2014:482678. doi: 10.1155/2014/482678. Epub 2014 Feb 23.

DOI:10.1155/2014/482678
PMID:24707487
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3953505/
Abstract

Kinetic resolution of 1-phenyl-2-propyn-1-ol, an important chiral synthon, was studied through trans-esterification with acyl acetate to investigate synergism between microwave irradiation and enzyme catalysis. Lipases from different microbial origins were employed for the kinetic resolution of (R/S)-1-phenyl-2-propyn-1-ol, among which Candida antarctica lipase B, immobilized on acrylic resin (Novozym 435), was found to be the best catalyst in n-hexane as solvent. Vinyl acetate was the most effective among different acyl esters studied. The effect of various parameters was studied in a systematic manner. Definite synergism between microwave and enzyme was observed. The initial rate was improved around 1.28 times under microwave irradiation than conventional heating. Under optimum conditions, maximum conversion (48.78%) and high enantiomeric excess (93.25%) were obtained in 2 h. From modeling studies, it is concluded that the reaction follows the Ping-Pong bi-bi mechanism with dead end alcohol inhibition. Kinetic parameters were obtained by using nonlinear regression. This process is green, clean, and easily scalable as compared to the chemical process.

摘要

对重要的手性合成子1-苯基-2-丙炔-1-醇进行动力学拆分，通过与乙酸酰基酯进行酯交换反应来研究微波辐射与酶催化之间的协同作用。使用来自不同微生物来源的脂肪酶对（R/S）-1-苯基-2-丙炔-1-醇进行动力学拆分，其中固定在丙烯酸树脂上的南极假丝酵母脂肪酶B（诺维信435）被发现是正己烷作为溶剂时的最佳催化剂。在研究的不同酰基酯中，乙酸乙烯酯最为有效。系统地研究了各种参数的影响。观察到微波与酶之间存在明显的协同作用。微波辐射下的初始速率比传统加热提高了约1.28倍。在最佳条件下，2小时内可获得最大转化率（48.78%）和高对映体过量（93.25%）。通过建模研究得出，该反应遵循乒乓双底物双产物机制，存在终产物醇抑制。通过非线性回归获得动力学参数。与化学过程相比，该过程绿色、清洁且易于放大。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/04cb381850ea/BMRI2014-482678.010.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/d5520c004254/BMRI2014-482678.002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/700837509114/BMRI2014-482678.003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/dfba4f1fb3aa/BMRI2014-482678.004.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/101e40e15813/BMRI2014-482678.009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/04cb381850ea/BMRI2014-482678.010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/b4cebbb2bc20/BMRI2014-482678.sch.001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/7e5796a0b8ed/BMRI2014-482678.001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/d5520c004254/BMRI2014-482678.002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/700837509114/BMRI2014-482678.003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/dfba4f1fb3aa/BMRI2014-482678.004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/efa825078ea7/BMRI2014-482678.005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/e53dbb5fe6c0/BMRI2014-482678.006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/0cdb3a683d8b/BMRI2014-482678.007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/052f184359fe/BMRI2014-482678.008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/101e40e15813/BMRI2014-482678.009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfcf/3953505/04cb381850ea/BMRI2014-482678.010.jpg

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