An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers
Schmidt S, Scherkus C, Muschiol J, et al. An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers. Angewandte Chemie (International ed. in English) . 2015;54(9):2784-2787. Poly-ε-caprolactone (PCL) is chemically produced on an industrial scale in spite of the need for hazardous peracetic aci...
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ftubbiepub:oai:pub.uni-bielefeld.de:2721884 2023-05-15T13:33:31+02:00 An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers Schmidt, Sandy Scherkus, Christian Muschiol, Jan Menyes, Ulf Winkler, Till Hummel, Werner Gröger, Harald Liese, Andreas Herz, Hans-Georg Bornscheuer, Uwe T. 2015 https://pub.uni-bielefeld.de/record/2721884 eng eng Wiley info:eu-repo/semantics/altIdentifier/doi/10.1002/anie.201410633 info:eu-repo/semantics/altIdentifier/issn/1521-3773 info:eu-repo/semantics/altIdentifier/wos/000350151000040 info:eu-repo/semantics/altIdentifier/pmid/25597635 https://pub.uni-bielefeld.de/record/2721884 info:eu-repo/semantics/closedAccess http://purl.org/coar/resource_type/c_6501 info:eu-repo/semantics/article doc-type:article text 2015 ftubbiepub https://doi.org/10.1002/anie.201410633 2022-02-08T22:32:17Z Schmidt S, Scherkus C, Muschiol J, et al. An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers. Angewandte Chemie (International ed. in English) . 2015;54(9):2784-2787. Poly-ε-caprolactone (PCL) is chemically produced on an industrial scale in spite of the need for hazardous peracetic acid as an oxidation reagent. Although Baeyer-Villiger monooxygenases (BVMO) in principle enable the enzymatic synthesis of ε-caprolactone (ε-CL) directly from cyclohexanone with molecular oxygen, current systems suffer from low productivity and are subject to substrate and product inhibition. The major limitations for such a biocatalytic route to produce this bulk chemical were overcome by combining an alcohol dehydrogenase with a BVMO to enable the efficient oxidation of cyclohexanol to ε-CL. Key to success was a subsequent direct ring-opening oligomerization of in situ formed ε-CL in the aqueous phase by using lipase A from Candida antarctica, thus efficiently solving the product inhibition problem and leading to the formation of oligo-ε-CL at more than 20 g L(-1) when starting from 200 mM cyclohexanol. This oligomer is easily chemically polymerized to PCL. Article in Journal/Newspaper Antarc* Antarctica PUB - Publications at Bielefeld University Angewandte Chemie International Edition 54 9 2784 2787 |
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PUB - Publications at Bielefeld University |
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ftubbiepub |
language |
English |
description |
Schmidt S, Scherkus C, Muschiol J, et al. An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers. Angewandte Chemie (International ed. in English) . 2015;54(9):2784-2787. Poly-ε-caprolactone (PCL) is chemically produced on an industrial scale in spite of the need for hazardous peracetic acid as an oxidation reagent. Although Baeyer-Villiger monooxygenases (BVMO) in principle enable the enzymatic synthesis of ε-caprolactone (ε-CL) directly from cyclohexanone with molecular oxygen, current systems suffer from low productivity and are subject to substrate and product inhibition. The major limitations for such a biocatalytic route to produce this bulk chemical were overcome by combining an alcohol dehydrogenase with a BVMO to enable the efficient oxidation of cyclohexanol to ε-CL. Key to success was a subsequent direct ring-opening oligomerization of in situ formed ε-CL in the aqueous phase by using lipase A from Candida antarctica, thus efficiently solving the product inhibition problem and leading to the formation of oligo-ε-CL at more than 20 g L(-1) when starting from 200 mM cyclohexanol. This oligomer is easily chemically polymerized to PCL. |
format |
Article in Journal/Newspaper |
author |
Schmidt, Sandy Scherkus, Christian Muschiol, Jan Menyes, Ulf Winkler, Till Hummel, Werner Gröger, Harald Liese, Andreas Herz, Hans-Georg Bornscheuer, Uwe T. |
spellingShingle |
Schmidt, Sandy Scherkus, Christian Muschiol, Jan Menyes, Ulf Winkler, Till Hummel, Werner Gröger, Harald Liese, Andreas Herz, Hans-Georg Bornscheuer, Uwe T. An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers |
author_facet |
Schmidt, Sandy Scherkus, Christian Muschiol, Jan Menyes, Ulf Winkler, Till Hummel, Werner Gröger, Harald Liese, Andreas Herz, Hans-Georg Bornscheuer, Uwe T. |
author_sort |
Schmidt, Sandy |
title |
An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers |
title_short |
An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers |
title_full |
An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers |
title_fullStr |
An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers |
title_full_unstemmed |
An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers |
title_sort |
enzyme cascade synthesis of ε-caprolactone and its oligomers |
publisher |
Wiley |
publishDate |
2015 |
url |
https://pub.uni-bielefeld.de/record/2721884 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1002/anie.201410633 info:eu-repo/semantics/altIdentifier/issn/1521-3773 info:eu-repo/semantics/altIdentifier/wos/000350151000040 info:eu-repo/semantics/altIdentifier/pmid/25597635 https://pub.uni-bielefeld.de/record/2721884 |
op_rights |
info:eu-repo/semantics/closedAccess |
op_doi |
https://doi.org/10.1002/anie.201410633 |
container_title |
Angewandte Chemie International Edition |
container_volume |
54 |
container_issue |
9 |
container_start_page |
2784 |
op_container_end_page |
2787 |
_version_ |
1766043120370188288 |