Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide
Herein, an efficient epoxidation of 1-nonene is described. In a simple epoxidation system, commercially available Novozym 435, an immobilized Candida antarctica lipase B, and hydrogen peroxide (H2O2) were utilized to facilitate the in situ oxidation of phenylacetic acid to the corresponding peroxy a...
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ftpubmed:oai:pubmedcentral.nih.gov:3497317 2023-05-15T13:32:54+02:00 Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide Abdulmalek, Emilia Arumugam, Mahashanon Basri, Mahiran Rahman, Mohd Basyaruddin Abdul 2012-10-12 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3497317 http://www.ncbi.nlm.nih.gov/pubmed/23202943 https://doi.org/10.3390/ijms131013140 en eng Molecular Diversity Preservation International (MDPI) http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3497317 http://www.ncbi.nlm.nih.gov/pubmed/23202943 http://dx.doi.org/10.3390/ijms131013140 © 2012 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0 This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0). CC-BY Article Text 2012 ftpubmed https://doi.org/10.3390/ijms131013140 2013-09-04T15:52:52Z Herein, an efficient epoxidation of 1-nonene is described. In a simple epoxidation system, commercially available Novozym 435, an immobilized Candida antarctica lipase B, and hydrogen peroxide (H2O2) were utilized to facilitate the in situ oxidation of phenylacetic acid to the corresponding peroxy acid which then reacted with 1-nonene to give 1-nonene oxide with high yield and selectivity. The aliphatic terminal alkene was epoxidised efficiently in chloroform to give an excellent yield (97%–99%) under the optimum reaction conditions, including temperature (35 °C), initial H2O2 concentration (30%), H2O2 amount (4.4 mmol), H2O2 addition rate (one step), acid amount (8.8 mmol), and stirring speed (250 rpm). Interestingly, the enzyme was stable under the single-step addition of H2O2 with a catalytic activity of 190.0 Ug−1. The entire epoxidation process was carried out within 12 h using a conventional water bath shaker. Text Antarc* Antarctica PubMed Central (PMC) International Journal of Molecular Sciences 13 12 13140 13149 |
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Article Abdulmalek, Emilia Arumugam, Mahashanon Basri, Mahiran Rahman, Mohd Basyaruddin Abdul Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide |
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Article |
description |
Herein, an efficient epoxidation of 1-nonene is described. In a simple epoxidation system, commercially available Novozym 435, an immobilized Candida antarctica lipase B, and hydrogen peroxide (H2O2) were utilized to facilitate the in situ oxidation of phenylacetic acid to the corresponding peroxy acid which then reacted with 1-nonene to give 1-nonene oxide with high yield and selectivity. The aliphatic terminal alkene was epoxidised efficiently in chloroform to give an excellent yield (97%–99%) under the optimum reaction conditions, including temperature (35 °C), initial H2O2 concentration (30%), H2O2 amount (4.4 mmol), H2O2 addition rate (one step), acid amount (8.8 mmol), and stirring speed (250 rpm). Interestingly, the enzyme was stable under the single-step addition of H2O2 with a catalytic activity of 190.0 Ug−1. The entire epoxidation process was carried out within 12 h using a conventional water bath shaker. |
format |
Text |
author |
Abdulmalek, Emilia Arumugam, Mahashanon Basri, Mahiran Rahman, Mohd Basyaruddin Abdul |
author_facet |
Abdulmalek, Emilia Arumugam, Mahashanon Basri, Mahiran Rahman, Mohd Basyaruddin Abdul |
author_sort |
Abdulmalek, Emilia |
title |
Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide |
title_short |
Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide |
title_full |
Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide |
title_fullStr |
Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide |
title_full_unstemmed |
Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide |
title_sort |
optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide |
publisher |
Molecular Diversity Preservation International (MDPI) |
publishDate |
2012 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3497317 http://www.ncbi.nlm.nih.gov/pubmed/23202943 https://doi.org/10.3390/ijms131013140 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3497317 http://www.ncbi.nlm.nih.gov/pubmed/23202943 http://dx.doi.org/10.3390/ijms131013140 |
op_rights |
© 2012 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0 This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0). |
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CC-BY |
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https://doi.org/10.3390/ijms131013140 |
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International Journal of Molecular Sciences |
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13 |
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12 |
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13140 |
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13149 |
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1766036869253955584 |