Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O‐Heterocycles from Allenes
Abstract Lipase/metal nanobiohybrids, generated by growth of silver or gold nanoparticles on protein matrixes are used as highly effective dual‐activity heterogeneous catalysts for the production of enantiomerically enriched 2,5‐dihydrofurans from allenic acetates in a one‐pot cascade process combin...
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Online Access: | http://dx.doi.org/10.1002/cctc.202200362 https://onlinelibrary.wiley.com/doi/pdf/10.1002/cctc.202200362 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/cctc.202200362 |
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crwiley:10.1002/cctc.202200362 2024-09-15T17:43:05+00:00 Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O‐Heterocycles from Allenes Naapuri, Janne M. Losada‐Garcia, Noelia Rothemann, Robin Alexander Pichardo, Manuel Carmona Prechtl, Martin H. G. Palomo, Jose M. Deska, Jan European Research Council Academy of Finland Suomen Kulttuurirahasto 2022 http://dx.doi.org/10.1002/cctc.202200362 https://onlinelibrary.wiley.com/doi/pdf/10.1002/cctc.202200362 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/cctc.202200362 en eng Wiley http://creativecommons.org/licenses/by-nc/4.0/ ChemCatChem volume 14, issue 16 ISSN 1867-3880 1867-3899 journal-article 2022 crwiley https://doi.org/10.1002/cctc.202200362 2024-08-01T04:21:30Z Abstract Lipase/metal nanobiohybrids, generated by growth of silver or gold nanoparticles on protein matrixes are used as highly effective dual‐activity heterogeneous catalysts for the production of enantiomerically enriched 2,5‐dihydrofurans from allenic acetates in a one‐pot cascade process combining a lipase‐mediated hydrolytic kinetic resolution with a metal‐catalyzed allene cycloisomerization. Incorporating a novel strategy based on enzyme‐polymer bioconjugates in the nanobiohybrid preparation enables excellent conversions in the process. Candida antarctica lipase B (CALB) in combination with a dextran‐based polymer modifier (DexAsp) proved to be most efficient when merged with silver nanoparticles. A range of hybrid materials were produced, combining Ag or Au metals with Thermomyces lanuginosus lipase (TLL) or CALB and its DexAsp or polyethyleneimine polymer bioconjugates. The wider applicability of the biohybrids is demonstrated by their use in allenic alcohol cyclizations, where a variety of dihydrofurans are obtained using a CALB/gold nanomaterial. These results underline the potential of the nanobiohybrid catalysis as promising approach to intricate one‐pot synthetic strategies. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library ChemCatChem 14 16 |
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Wiley Online Library |
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English |
description |
Abstract Lipase/metal nanobiohybrids, generated by growth of silver or gold nanoparticles on protein matrixes are used as highly effective dual‐activity heterogeneous catalysts for the production of enantiomerically enriched 2,5‐dihydrofurans from allenic acetates in a one‐pot cascade process combining a lipase‐mediated hydrolytic kinetic resolution with a metal‐catalyzed allene cycloisomerization. Incorporating a novel strategy based on enzyme‐polymer bioconjugates in the nanobiohybrid preparation enables excellent conversions in the process. Candida antarctica lipase B (CALB) in combination with a dextran‐based polymer modifier (DexAsp) proved to be most efficient when merged with silver nanoparticles. A range of hybrid materials were produced, combining Ag or Au metals with Thermomyces lanuginosus lipase (TLL) or CALB and its DexAsp or polyethyleneimine polymer bioconjugates. The wider applicability of the biohybrids is demonstrated by their use in allenic alcohol cyclizations, where a variety of dihydrofurans are obtained using a CALB/gold nanomaterial. These results underline the potential of the nanobiohybrid catalysis as promising approach to intricate one‐pot synthetic strategies. |
author2 |
European Research Council Academy of Finland Suomen Kulttuurirahasto |
format |
Article in Journal/Newspaper |
author |
Naapuri, Janne M. Losada‐Garcia, Noelia Rothemann, Robin Alexander Pichardo, Manuel Carmona Prechtl, Martin H. G. Palomo, Jose M. Deska, Jan |
spellingShingle |
Naapuri, Janne M. Losada‐Garcia, Noelia Rothemann, Robin Alexander Pichardo, Manuel Carmona Prechtl, Martin H. G. Palomo, Jose M. Deska, Jan Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O‐Heterocycles from Allenes |
author_facet |
Naapuri, Janne M. Losada‐Garcia, Noelia Rothemann, Robin Alexander Pichardo, Manuel Carmona Prechtl, Martin H. G. Palomo, Jose M. Deska, Jan |
author_sort |
Naapuri, Janne M. |
title |
Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O‐Heterocycles from Allenes |
title_short |
Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O‐Heterocycles from Allenes |
title_full |
Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O‐Heterocycles from Allenes |
title_fullStr |
Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O‐Heterocycles from Allenes |
title_full_unstemmed |
Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O‐Heterocycles from Allenes |
title_sort |
cascade catalysis through bifunctional lipase metal biohybrids for the synthesis of enantioenriched o‐heterocycles from allenes |
publisher |
Wiley |
publishDate |
2022 |
url |
http://dx.doi.org/10.1002/cctc.202200362 https://onlinelibrary.wiley.com/doi/pdf/10.1002/cctc.202200362 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/cctc.202200362 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ChemCatChem volume 14, issue 16 ISSN 1867-3880 1867-3899 |
op_rights |
http://creativecommons.org/licenses/by-nc/4.0/ |
op_doi |
https://doi.org/10.1002/cctc.202200362 |
container_title |
ChemCatChem |
container_volume |
14 |
container_issue |
16 |
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1810489906263228416 |