Solvent screening, optimization and kinetic parameters of the biocatalytic epoxidation reaction of β-pinene mediated by Novozym®435
Fundação de Amparo à Pesquisa do Estado do Rio de Janeiro (FAPERJ) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) FAPERJ: 201.511/2018 CAPES: 88881.068489/2014-01 FAPERJ: E-26/200.183/2019 FAPERJ: E-26/202.728/2018 Monoterpenes, such as beta-pinene, are secondary metabolites wid...
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Online Access: | http://hdl.handle.net/11449/240271 https://doi.org/10.1007/s10529-022-03265-8 |
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ftunivespir:oai:repositorio.unesp.br:11449/240271 2023-07-02T03:30:41+02:00 Solvent screening, optimization and kinetic parameters of the biocatalytic epoxidation reaction of β-pinene mediated by Novozym®435 Martins, Gustavo dos Santos Staudt, Amanda Sutili, Felipe Korbus Malafaia, Camila Rodrigues Adão Leal, Ivana Correa Ramos Universidade Estadual Paulista (UNESP) 2022-07-01 867-878 http://hdl.handle.net/11449/240271 https://doi.org/10.1007/s10529-022-03265-8 eng eng Biotechnology Letters http://dx.doi.org/10.1007/s10529-022-03265-8 Biotechnology Letters, v. 44, n. 7, p. 867-878, 2022. 1573-6776 0141-5492 http://hdl.handle.net/11449/240271 doi:10.1007/s10529-022-03265-8 2-s2.0-85132201713 Beta-pinene Biocatalysis Epoxidation Experimental design Lipase Novozym 435 info:eu-repo/semantics/article 2022 ftunivespir https://doi.org/10.1007/s10529-022-03265-8 2023-06-12T17:45:03Z Fundação de Amparo à Pesquisa do Estado do Rio de Janeiro (FAPERJ) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) FAPERJ: 201.511/2018 CAPES: 88881.068489/2014-01 FAPERJ: E-26/200.183/2019 FAPERJ: E-26/202.728/2018 Monoterpenes, such as beta-pinene, are secondary metabolites widely used in the flavors and fragrance industries and can have their structure altered to enhance their applicability, such as producing epoxides, which are used as intermediaries for pharmaceuticals. Epoxides are commonly synthesized by the use of inorganic acids as catalysts, although the acid medium induces epoxide degradation. To overcome these limitations biocatalysis is shown as an alternative. Related to, this work aimed to perform the synthesis of β-Pinene epoxide using Pseudozyma antarctica lipase B (Novozym®435) as a biocatalyst, while determining the independent variables that influence the reaction using experimental design tools. Different solvent systems were evaluated (cyclohexane, acetonitrile, ethyl acetate, and dichloromethane) until 72 h reaction time, from which ethyl acetate showed higher conversion into the epoxidized product (40% in 24 h). Under the other solvents systems, several oxidized by-products were obtained, such as ketones and aldehydes. Moreover, applying metrics of green chemistry, ethyl acetate was also corroborated as the most promising solvent, with a higher atom economy (66.8%) in comparison to the others (41.3%), and a smaller E-value (1.19). Ethyl acetate was the solvent/acyl donor of choice and had the molar ratio and percentage of biocatalyst increased, which resulted in 80% of the product after 3 h of reaction. To obtain an optimized model, four independent variables (temperature, stirring, molar ratio, percentage of biocatalyst) were evaluated using experimental design tools, Fractional Factorial Design and Central Composite Rotatable Design, with conversions ranging from 23 to 95% after 3 h. All the independent variables were statistically significant (p < ... Article in Journal/Newspaper Antarc* Antarctica Universidade Estadual Paulista São Paulo: Repositório Institucional UNESP Biotechnology Letters 44 7 867 878 |
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Open Polar |
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Universidade Estadual Paulista São Paulo: Repositório Institucional UNESP |
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ftunivespir |
language |
English |
topic |
Beta-pinene Biocatalysis Epoxidation Experimental design Lipase Novozym 435 |
spellingShingle |
Beta-pinene Biocatalysis Epoxidation Experimental design Lipase Novozym 435 Martins, Gustavo dos Santos Staudt, Amanda Sutili, Felipe Korbus Malafaia, Camila Rodrigues Adão Leal, Ivana Correa Ramos Solvent screening, optimization and kinetic parameters of the biocatalytic epoxidation reaction of β-pinene mediated by Novozym®435 |
topic_facet |
Beta-pinene Biocatalysis Epoxidation Experimental design Lipase Novozym 435 |
description |
Fundação de Amparo à Pesquisa do Estado do Rio de Janeiro (FAPERJ) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) FAPERJ: 201.511/2018 CAPES: 88881.068489/2014-01 FAPERJ: E-26/200.183/2019 FAPERJ: E-26/202.728/2018 Monoterpenes, such as beta-pinene, are secondary metabolites widely used in the flavors and fragrance industries and can have their structure altered to enhance their applicability, such as producing epoxides, which are used as intermediaries for pharmaceuticals. Epoxides are commonly synthesized by the use of inorganic acids as catalysts, although the acid medium induces epoxide degradation. To overcome these limitations biocatalysis is shown as an alternative. Related to, this work aimed to perform the synthesis of β-Pinene epoxide using Pseudozyma antarctica lipase B (Novozym®435) as a biocatalyst, while determining the independent variables that influence the reaction using experimental design tools. Different solvent systems were evaluated (cyclohexane, acetonitrile, ethyl acetate, and dichloromethane) until 72 h reaction time, from which ethyl acetate showed higher conversion into the epoxidized product (40% in 24 h). Under the other solvents systems, several oxidized by-products were obtained, such as ketones and aldehydes. Moreover, applying metrics of green chemistry, ethyl acetate was also corroborated as the most promising solvent, with a higher atom economy (66.8%) in comparison to the others (41.3%), and a smaller E-value (1.19). Ethyl acetate was the solvent/acyl donor of choice and had the molar ratio and percentage of biocatalyst increased, which resulted in 80% of the product after 3 h of reaction. To obtain an optimized model, four independent variables (temperature, stirring, molar ratio, percentage of biocatalyst) were evaluated using experimental design tools, Fractional Factorial Design and Central Composite Rotatable Design, with conversions ranging from 23 to 95% after 3 h. All the independent variables were statistically significant (p < ... |
author2 |
Universidade Estadual Paulista (UNESP) |
format |
Article in Journal/Newspaper |
author |
Martins, Gustavo dos Santos Staudt, Amanda Sutili, Felipe Korbus Malafaia, Camila Rodrigues Adão Leal, Ivana Correa Ramos |
author_facet |
Martins, Gustavo dos Santos Staudt, Amanda Sutili, Felipe Korbus Malafaia, Camila Rodrigues Adão Leal, Ivana Correa Ramos |
author_sort |
Martins, Gustavo dos Santos |
title |
Solvent screening, optimization and kinetic parameters of the biocatalytic epoxidation reaction of β-pinene mediated by Novozym®435 |
title_short |
Solvent screening, optimization and kinetic parameters of the biocatalytic epoxidation reaction of β-pinene mediated by Novozym®435 |
title_full |
Solvent screening, optimization and kinetic parameters of the biocatalytic epoxidation reaction of β-pinene mediated by Novozym®435 |
title_fullStr |
Solvent screening, optimization and kinetic parameters of the biocatalytic epoxidation reaction of β-pinene mediated by Novozym®435 |
title_full_unstemmed |
Solvent screening, optimization and kinetic parameters of the biocatalytic epoxidation reaction of β-pinene mediated by Novozym®435 |
title_sort |
solvent screening, optimization and kinetic parameters of the biocatalytic epoxidation reaction of β-pinene mediated by novozym®435 |
publishDate |
2022 |
url |
http://hdl.handle.net/11449/240271 https://doi.org/10.1007/s10529-022-03265-8 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
Biotechnology Letters http://dx.doi.org/10.1007/s10529-022-03265-8 Biotechnology Letters, v. 44, n. 7, p. 867-878, 2022. 1573-6776 0141-5492 http://hdl.handle.net/11449/240271 doi:10.1007/s10529-022-03265-8 2-s2.0-85132201713 |
op_doi |
https://doi.org/10.1007/s10529-022-03265-8 |
container_title |
Biotechnology Letters |
container_volume |
44 |
container_issue |
7 |
container_start_page |
867 |
op_container_end_page |
878 |
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1770274938417053696 |