Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O-Heterocycles from Allenes
Loading...
Access rights
openAccess
publishedVersion
URL
Journal Title
Journal ISSN
Volume Title
A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
This publication is imported from Aalto University research portal.
View publication in the Research portal (opens in new window)
View/Open full text file from the Research portal (opens in new window)
View publication in the Research portal (opens in new window)
View/Open full text file from the Research portal (opens in new window)
Date
Major/Subject
Mcode
Degree programme
Language
en
Pages
Series
ChemCatChem, Volume 14, issue 16
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.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.
Keywords
Other note
Citation
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