Biocatalytic production of a Nylon 6 precursor from caprolactone in continuous flow.
6-aminocaproic acid (6ACA) is a key building block and an attractive precursor of caprolactam, which is used to synthesize nylon-6, one of the most common polymers manufactured nowadays. (Bio)-production of platform chemicals from renewable feedstocks is instrumental to tackle climate change and dec...
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ftunivbern:oai:boris.unibe.ch:170501 2023-08-20T04:00:44+02:00 Biocatalytic production of a Nylon 6 precursor from caprolactone in continuous flow. Romero-Fernandez, Maria Heckmann, Christian M Paradisi, Francesca 2022-08-19 application/pdf https://boris.unibe.ch/170501/1/ChemSusChem_-_2022_-_Romero-Fernandez_-_Biocatalytic_production_of_a_Nylon_6_precursor_from_caprolactone_in_continuous_flow.pdf https://boris.unibe.ch/170501/ eng eng Wiley https://boris.unibe.ch/170501/ info:eu-repo/semantics/openAccess Romero-Fernandez, Maria; Heckmann, Christian M; Paradisi, Francesca (2022). Biocatalytic production of a Nylon 6 precursor from caprolactone in continuous flow. ChemSusChem, 15(16), e202200811. Wiley 10.1002/cssc.202200811 <http://dx.doi.org/10.1002/cssc.202200811> 570 Life sciences biology 540 Chemistry info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion PeerReviewed 2022 ftunivbern https://doi.org/10.1002/cssc.202200811 2023-07-31T22:14:40Z 6-aminocaproic acid (6ACA) is a key building block and an attractive precursor of caprolactam, which is used to synthesize nylon-6, one of the most common polymers manufactured nowadays. (Bio)-production of platform chemicals from renewable feedstocks is instrumental to tackle climate change and decrease fossil fuel dependence. Here, we report the cell-free biosynthesis of 6ACA from 6-hydroxycaproic acid using a co-immobilised multienzyme system based on horse liver alcohol dehydrogenase, Halomonas elongata transaminase, and Lactobacillus pentosus NADH oxidase for in-situ cofactor recycling, with >90% molar conversion (m. c.) The integration of a step to synthesize hydroxy-acid from lactone by immobilised Candida antarctica lipase B resulted in >80% m. c. of ε-caprolactone to 6ACA, >20% of δ-valerolactone to 5-aminovaleric acid, and 30% of γ-butyrolactone to gamma-aminobutyric acid, in one-pot batch reactions. Two serial packed-bed reactors were set-up using these biocatalysts and applied to the continuous flow synthesis of 6ACA from ε-caprolactone, achieving a space-time yield of up to 3.31 g 6ACA h -1 L -1 with a segmented liquid/air flow for constant oxygen supply. Article in Journal/Newspaper Antarc* Antarctica BORIS (Bern Open Repository and Information System, University of Bern) ChemSusChem |
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BORIS (Bern Open Repository and Information System, University of Bern) |
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ftunivbern |
language |
English |
topic |
570 Life sciences biology 540 Chemistry |
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570 Life sciences biology 540 Chemistry Romero-Fernandez, Maria Heckmann, Christian M Paradisi, Francesca Biocatalytic production of a Nylon 6 precursor from caprolactone in continuous flow. |
topic_facet |
570 Life sciences biology 540 Chemistry |
description |
6-aminocaproic acid (6ACA) is a key building block and an attractive precursor of caprolactam, which is used to synthesize nylon-6, one of the most common polymers manufactured nowadays. (Bio)-production of platform chemicals from renewable feedstocks is instrumental to tackle climate change and decrease fossil fuel dependence. Here, we report the cell-free biosynthesis of 6ACA from 6-hydroxycaproic acid using a co-immobilised multienzyme system based on horse liver alcohol dehydrogenase, Halomonas elongata transaminase, and Lactobacillus pentosus NADH oxidase for in-situ cofactor recycling, with >90% molar conversion (m. c.) The integration of a step to synthesize hydroxy-acid from lactone by immobilised Candida antarctica lipase B resulted in >80% m. c. of ε-caprolactone to 6ACA, >20% of δ-valerolactone to 5-aminovaleric acid, and 30% of γ-butyrolactone to gamma-aminobutyric acid, in one-pot batch reactions. Two serial packed-bed reactors were set-up using these biocatalysts and applied to the continuous flow synthesis of 6ACA from ε-caprolactone, achieving a space-time yield of up to 3.31 g 6ACA h -1 L -1 with a segmented liquid/air flow for constant oxygen supply. |
format |
Article in Journal/Newspaper |
author |
Romero-Fernandez, Maria Heckmann, Christian M Paradisi, Francesca |
author_facet |
Romero-Fernandez, Maria Heckmann, Christian M Paradisi, Francesca |
author_sort |
Romero-Fernandez, Maria |
title |
Biocatalytic production of a Nylon 6 precursor from caprolactone in continuous flow. |
title_short |
Biocatalytic production of a Nylon 6 precursor from caprolactone in continuous flow. |
title_full |
Biocatalytic production of a Nylon 6 precursor from caprolactone in continuous flow. |
title_fullStr |
Biocatalytic production of a Nylon 6 precursor from caprolactone in continuous flow. |
title_full_unstemmed |
Biocatalytic production of a Nylon 6 precursor from caprolactone in continuous flow. |
title_sort |
biocatalytic production of a nylon 6 precursor from caprolactone in continuous flow. |
publisher |
Wiley |
publishDate |
2022 |
url |
https://boris.unibe.ch/170501/1/ChemSusChem_-_2022_-_Romero-Fernandez_-_Biocatalytic_production_of_a_Nylon_6_precursor_from_caprolactone_in_continuous_flow.pdf https://boris.unibe.ch/170501/ |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Romero-Fernandez, Maria; Heckmann, Christian M; Paradisi, Francesca (2022). Biocatalytic production of a Nylon 6 precursor from caprolactone in continuous flow. ChemSusChem, 15(16), e202200811. Wiley 10.1002/cssc.202200811 <http://dx.doi.org/10.1002/cssc.202200811> |
op_relation |
https://boris.unibe.ch/170501/ |
op_rights |
info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.1002/cssc.202200811 |
container_title |
ChemSusChem |
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1774719990362013696 |