Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O-Heterocycles from Allenes
| openaire: EC/H2020/865885/EU//ABIONYS Funding Information: We gratefully acknowledge financial support by the European Research Council (ABIONYS, 865885), the Academy of Finland (grant numbers 298250 and 324976), the COST action CA15106 (CHAOS), the Ruth & Nils‐Erik Stenbäcks Stiftelse, and th...
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WILEY-V C H VERLAG GMBH
2022
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Online Access: | https://aaltodoc.aalto.fi/handle/123456789/115674 https://doi.org/10.1002/cctc.202200362 |
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Aalto University Publication Archive (Aaltodoc) |
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English |
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cascades dual catalysis heterocycles lipases nanoparticles |
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cascades dual catalysis heterocycles lipases nanoparticles Naapuri, Janne M. Losada-Garcia, Noelia Rothemann, Robin Alexander Carmona Pichardo, Manuel 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 |
topic_facet |
cascades dual catalysis heterocycles lipases nanoparticles |
description |
| openaire: EC/H2020/865885/EU//ABIONYS Funding Information: We gratefully acknowledge financial support by the European Research Council (ABIONYS, 865885), the Academy of Finland (grant numbers 298250 and 324976), the COST action CA15106 (CHAOS), the Ruth & Nils‐Erik Stenbäcks Stiftelse, and the Finnish Cultural Foundation. The authors thank the support by the Spanish National Research Council (CSIC) and the Portuguese Research Foundation (EXPL/QUI‐QOR/1079/2021). Publisher Copyright: © 2022 The Authors. ChemCatChem published by Wiley-VCH GmbH. 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. Peer reviewed |
author2 |
Department of Chemistry and Materials Science Bioorganic chemistry CSIC - Institute of Catalysis and Petrochemistry Universidade Lisboa Aalto-yliopisto Aalto University |
format |
Article in Journal/Newspaper |
author |
Naapuri, Janne M. Losada-Garcia, Noelia Rothemann, Robin Alexander Carmona Pichardo, Manuel Prechtl, Martin H.G. Palomo, Jose M. Deska, Jan |
author_facet |
Naapuri, Janne M. Losada-Garcia, Noelia Rothemann, Robin Alexander Carmona Pichardo, Manuel 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-V C H VERLAG GMBH |
publishDate |
2022 |
url |
https://aaltodoc.aalto.fi/handle/123456789/115674 https://doi.org/10.1002/cctc.202200362 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/grantAgreement/EC/H2020/865885/EU//ABIONYS Funding Information: We gratefully acknowledge financial support by the European Research Council (ABIONYS, 865885), the Academy of Finland (grant numbers 298250 and 324976), the COST action CA15106 (CHAOS), the Ruth & Nils‐Erik Stenbäcks Stiftelse, and the Finnish Cultural Foundation. The authors thank the support by the Spanish National Research Council (CSIC) and the Portuguese Research Foundation (EXPL/QUI‐QOR/1079/2021). Publisher Copyright: © 2022 The Authors. ChemCatChem published by Wiley-VCH GmbH. ChemCatChem articlenumber 202200362 Naapuri, J M, Losada-Garcia, N, Rothemann, R A, Carmona Pichardo, M, Prechtl, M H G, Palomo, J M & Deska, J 2022, ' Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O-Heterocycles from Allenes ', ChemCatChem, vol. 14, no. 16, 202200362 . https://doi.org/10.1002/cctc.202200362 1867-3880 PURE UUID: 1361af77-f3d1-48e5-868b-72a1ddc3a735 PURE ITEMURL: https://research.aalto.fi/en/publications/1361af77-f3d1-48e5-868b-72a1ddc3a735 PURE LINK: http://www.scopus.com/inward/record.url?scp=85132331402&partnerID=8YFLogxK PURE FILEURL: https://research.aalto.fi/files/87402251/Cascade_Catalysis_Through_Bifunctional_Lipase_Metal_Biohybrids_for_the_Synthesis_of_Enantioenriched_O_Heterocycles_from_Allenes.pdf https://aaltodoc.aalto.fi/handle/123456789/115674 URN:NBN:fi:aalto-202208104496 doi:10.1002/cctc.202200362 |
op_rights |
openAccess |
op_doi |
https://doi.org/10.1002/cctc.202200362 |
container_title |
ChemCatChem |
container_volume |
14 |
container_issue |
16 |
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ftaaltouniv:oai:aaltodoc.aalto.fi:123456789/115674 2024-04-28T07:56:51+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 Carmona Pichardo, Manuel Prechtl, Martin H.G. Palomo, Jose M. Deska, Jan Department of Chemistry and Materials Science Bioorganic chemistry CSIC - Institute of Catalysis and Petrochemistry Universidade Lisboa Aalto-yliopisto Aalto University 2022-08-19 application/pdf https://aaltodoc.aalto.fi/handle/123456789/115674 https://doi.org/10.1002/cctc.202200362 en eng WILEY-V C H VERLAG GMBH info:eu-repo/grantAgreement/EC/H2020/865885/EU//ABIONYS Funding Information: We gratefully acknowledge financial support by the European Research Council (ABIONYS, 865885), the Academy of Finland (grant numbers 298250 and 324976), the COST action CA15106 (CHAOS), the Ruth & Nils‐Erik Stenbäcks Stiftelse, and the Finnish Cultural Foundation. The authors thank the support by the Spanish National Research Council (CSIC) and the Portuguese Research Foundation (EXPL/QUI‐QOR/1079/2021). Publisher Copyright: © 2022 The Authors. ChemCatChem published by Wiley-VCH GmbH. ChemCatChem articlenumber 202200362 Naapuri, J M, Losada-Garcia, N, Rothemann, R A, Carmona Pichardo, M, Prechtl, M H G, Palomo, J M & Deska, J 2022, ' Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O-Heterocycles from Allenes ', ChemCatChem, vol. 14, no. 16, 202200362 . https://doi.org/10.1002/cctc.202200362 1867-3880 PURE UUID: 1361af77-f3d1-48e5-868b-72a1ddc3a735 PURE ITEMURL: https://research.aalto.fi/en/publications/1361af77-f3d1-48e5-868b-72a1ddc3a735 PURE LINK: http://www.scopus.com/inward/record.url?scp=85132331402&partnerID=8YFLogxK PURE FILEURL: https://research.aalto.fi/files/87402251/Cascade_Catalysis_Through_Bifunctional_Lipase_Metal_Biohybrids_for_the_Synthesis_of_Enantioenriched_O_Heterocycles_from_Allenes.pdf https://aaltodoc.aalto.fi/handle/123456789/115674 URN:NBN:fi:aalto-202208104496 doi:10.1002/cctc.202200362 openAccess cascades dual catalysis heterocycles lipases nanoparticles A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä 2022 ftaaltouniv https://doi.org/10.1002/cctc.202200362 2024-04-10T00:19:42Z | openaire: EC/H2020/865885/EU//ABIONYS Funding Information: We gratefully acknowledge financial support by the European Research Council (ABIONYS, 865885), the Academy of Finland (grant numbers 298250 and 324976), the COST action CA15106 (CHAOS), the Ruth & Nils‐Erik Stenbäcks Stiftelse, and the Finnish Cultural Foundation. The authors thank the support by the Spanish National Research Council (CSIC) and the Portuguese Research Foundation (EXPL/QUI‐QOR/1079/2021). Publisher Copyright: © 2022 The Authors. ChemCatChem published by Wiley-VCH GmbH. 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. Peer reviewed Article in Journal/Newspaper Antarc* Antarctica Aalto University Publication Archive (Aaltodoc) ChemCatChem 14 16 |