CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability
In this study, an immobilization strategy for magnetic cross-linking enzyme aggregates of lipase B from Candida antarctica (CALB) was developed and investigated. Magnetic particles were prepared by conventional co-precipitation. The magnetic nanoparticles were modified with 3-aminopropyltriethoxysil...
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ftdoajarticles:oai:doaj.org/article:45b573a0dad3473983b77ea541883bd1 2023-05-15T13:55:48+02:00 CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability Xiu Xing Jun-Qi Jia Jing-Fan Zhang Zi-Wen Zhou Jun Li Na Wang Xiao-Qi Yu 2019-01-01T00:00:00Z https://doi.org/10.3390/molecules24030490 https://doaj.org/article/45b573a0dad3473983b77ea541883bd1 EN eng MDPI AG https://www.mdpi.com/1420-3049/24/3/490 https://doaj.org/toc/1420-3049 1420-3049 doi:10.3390/molecules24030490 https://doaj.org/article/45b573a0dad3473983b77ea541883bd1 Molecules, Vol 24, Iss 3, p 490 (2019) CALB magnetic nanoparticles cross-linked enzyme aggregates resolution secondary alcohols Organic chemistry QD241-441 article 2019 ftdoajarticles https://doi.org/10.3390/molecules24030490 2022-12-30T21:15:46Z In this study, an immobilization strategy for magnetic cross-linking enzyme aggregates of lipase B from Candida antarctica (CALB) was developed and investigated. Magnetic particles were prepared by conventional co-precipitation. The magnetic nanoparticles were modified with 3-aminopropyltriethoxysilane (APTES) to obtain surface amino-functionalized magnetic nanoparticles (APTES⁻Fe 3 O 4 ) as immobilization materials. Glutaraldehyde was used as a crosslinker to covalently bind CALB to APTES⁻Fe 3 O 4 . The optimal conditions of immobilization of lipase and resolution of racemic 1-phenylethanol were investigated. Under optimal conditions, esters could be obtained with conversion of 50%, enantiomeric excess of product (ee p ) > 99%, enantiomeric excess of substrate (ee s ) > 99%, and enantiomeric ratio (E) > 1000. The magnetic CALB CLEAs were successfully used for enzymatic kinetic resolution of fifteen secondary alcohols. Compared with Novozym 435, the magnetic CALB CLEAs exhibited a better enantioselectivity for most substrates. The conversion was still greater than 49% after the magnetic CALB CLEAs had been reused 10 times in a 48 h reaction cycle; both ee s and ee p were close to 99%. Furthermore, there was little decrease in catalytic activity and enantioselectivity after being stored at −20 °C for 90 days. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Molecules 24 3 490 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
CALB magnetic nanoparticles cross-linked enzyme aggregates resolution secondary alcohols Organic chemistry QD241-441 |
spellingShingle |
CALB magnetic nanoparticles cross-linked enzyme aggregates resolution secondary alcohols Organic chemistry QD241-441 Xiu Xing Jun-Qi Jia Jing-Fan Zhang Zi-Wen Zhou Jun Li Na Wang Xiao-Qi Yu CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability |
topic_facet |
CALB magnetic nanoparticles cross-linked enzyme aggregates resolution secondary alcohols Organic chemistry QD241-441 |
description |
In this study, an immobilization strategy for magnetic cross-linking enzyme aggregates of lipase B from Candida antarctica (CALB) was developed and investigated. Magnetic particles were prepared by conventional co-precipitation. The magnetic nanoparticles were modified with 3-aminopropyltriethoxysilane (APTES) to obtain surface amino-functionalized magnetic nanoparticles (APTES⁻Fe 3 O 4 ) as immobilization materials. Glutaraldehyde was used as a crosslinker to covalently bind CALB to APTES⁻Fe 3 O 4 . The optimal conditions of immobilization of lipase and resolution of racemic 1-phenylethanol were investigated. Under optimal conditions, esters could be obtained with conversion of 50%, enantiomeric excess of product (ee p ) > 99%, enantiomeric excess of substrate (ee s ) > 99%, and enantiomeric ratio (E) > 1000. The magnetic CALB CLEAs were successfully used for enzymatic kinetic resolution of fifteen secondary alcohols. Compared with Novozym 435, the magnetic CALB CLEAs exhibited a better enantioselectivity for most substrates. The conversion was still greater than 49% after the magnetic CALB CLEAs had been reused 10 times in a 48 h reaction cycle; both ee s and ee p were close to 99%. Furthermore, there was little decrease in catalytic activity and enantioselectivity after being stored at −20 °C for 90 days. |
format |
Article in Journal/Newspaper |
author |
Xiu Xing Jun-Qi Jia Jing-Fan Zhang Zi-Wen Zhou Jun Li Na Wang Xiao-Qi Yu |
author_facet |
Xiu Xing Jun-Qi Jia Jing-Fan Zhang Zi-Wen Zhou Jun Li Na Wang Xiao-Qi Yu |
author_sort |
Xiu Xing |
title |
CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability |
title_short |
CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability |
title_full |
CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability |
title_fullStr |
CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability |
title_full_unstemmed |
CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability |
title_sort |
calb immobilized onto magnetic nanoparticles for efficient kinetic resolution of racemic secondary alcohols: long-term stability and reusability |
publisher |
MDPI AG |
publishDate |
2019 |
url |
https://doi.org/10.3390/molecules24030490 https://doaj.org/article/45b573a0dad3473983b77ea541883bd1 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Molecules, Vol 24, Iss 3, p 490 (2019) |
op_relation |
https://www.mdpi.com/1420-3049/24/3/490 https://doaj.org/toc/1420-3049 1420-3049 doi:10.3390/molecules24030490 https://doaj.org/article/45b573a0dad3473983b77ea541883bd1 |
op_doi |
https://doi.org/10.3390/molecules24030490 |
container_title |
Molecules |
container_volume |
24 |
container_issue |
3 |
container_start_page |
490 |
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1766262637250740224 |