Microwave Assisted Enzymatic Kinetic Resolution of (±)-1-Phenyl-2-propyn-1-ol in Nonaqueous Media
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...
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ftciteseerx:oai:CiteSeerX.psu:10.1.1.1074.1388 2023-05-15T14:04:21+02:00 Microwave Assisted Enzymatic Kinetic Resolution of (±)-1-Phenyl-2-propyn-1-ol in Nonaqueous Media Saravanan Devendran Ganapati D Yadav The Pennsylvania State University CiteSeerX Archives application/pdf http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1074.1388 http://downloads.hindawi.com/journals/bmri/2014/482678.pdf en eng http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1074.1388 http://downloads.hindawi.com/journals/bmri/2014/482678.pdf Metadata may be used without restrictions as long as the oai identifier remains attached to it. http://downloads.hindawi.com/journals/bmri/2014/482678.pdf text ftciteseerx 2020-04-26T00:27:09Z 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. Text Antarc* Antarctica Unknown |
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English |
description |
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. |
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The Pennsylvania State University CiteSeerX Archives |
format |
Text |
author |
Saravanan Devendran Ganapati D Yadav |
spellingShingle |
Saravanan Devendran Ganapati D Yadav Microwave Assisted Enzymatic Kinetic Resolution of (±)-1-Phenyl-2-propyn-1-ol in Nonaqueous Media |
author_facet |
Saravanan Devendran Ganapati D Yadav |
author_sort |
Saravanan Devendran |
title |
Microwave Assisted Enzymatic Kinetic Resolution of (±)-1-Phenyl-2-propyn-1-ol in Nonaqueous Media |
title_short |
Microwave Assisted Enzymatic Kinetic Resolution of (±)-1-Phenyl-2-propyn-1-ol in Nonaqueous Media |
title_full |
Microwave Assisted Enzymatic Kinetic Resolution of (±)-1-Phenyl-2-propyn-1-ol in Nonaqueous Media |
title_fullStr |
Microwave Assisted Enzymatic Kinetic Resolution of (±)-1-Phenyl-2-propyn-1-ol in Nonaqueous Media |
title_full_unstemmed |
Microwave Assisted Enzymatic Kinetic Resolution of (±)-1-Phenyl-2-propyn-1-ol in Nonaqueous Media |
title_sort |
microwave assisted enzymatic kinetic resolution of (±)-1-phenyl-2-propyn-1-ol in nonaqueous media |
url |
http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1074.1388 http://downloads.hindawi.com/journals/bmri/2014/482678.pdf |
genre |
Antarc* Antarctica |
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Antarc* Antarctica |
op_source |
http://downloads.hindawi.com/journals/bmri/2014/482678.pdf |
op_relation |
http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1074.1388 http://downloads.hindawi.com/journals/bmri/2014/482678.pdf |
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Metadata may be used without restrictions as long as the oai identifier remains attached to it. |
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