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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...

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Autores principales: Abdulmalek, Emilia, Arumugam, Mahashanon, Basri, Mahiran, Rahman, Mohd Basyaruddin Abdul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International (MDPI) 2012
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.
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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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