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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 (H(2)O(2)) were utilized to facilitate the in situ oxidation of phenylacetic acid to the corresponding pero...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Molecular Diversity Preservation International (MDPI)
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3497317/ https://www.ncbi.nlm.nih.gov/pubmed/23202943 http://dx.doi.org/10.3390/ijms131013140 |
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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 |
collection | PubMed |
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 (H(2)O(2)) 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 H(2)O(2) concentration (30%), H(2)O(2) amount (4.4 mmol), H(2)O(2) 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 H(2)O(2) 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 | Online Article Text |
id | pubmed-3497317 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | Molecular Diversity Preservation International (MDPI) |
record_format | MEDLINE/PubMed |
spelling | pubmed-34973172012-11-29 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 Int J Mol Sci Article 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 (H(2)O(2)) 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 H(2)O(2) concentration (30%), H(2)O(2) amount (4.4 mmol), H(2)O(2) 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 H(2)O(2) 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. Molecular Diversity Preservation International (MDPI) 2012-10-12 /pmc/articles/PMC3497317/ /pubmed/23202943 http://dx.doi.org/10.3390/ijms131013140 Text en © 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). |
spellingShingle | 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 |
title | 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_short | 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 |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3497317/ https://www.ncbi.nlm.nih.gov/pubmed/23202943 http://dx.doi.org/10.3390/ijms131013140 |
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