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Computational Studies Suggest Promiscuous Candida antarctica Lipase B as an Environmentally Friendly Alternative for the Production of Epoxides
dc.contributor.author | Galmés, Miquel À | |
dc.contributor.author | Świderek, Katarzyna | |
dc.contributor.author | Moliner, Vicent | |
dc.date.accessioned | 2021-10-08T06:56:40Z | |
dc.date.available | 2021-10-08T06:56:40Z | |
dc.date.issued | 2021-07-26 | |
dc.identifier.citation | Miquel A. Galmés, Katarzyna Świderek, and Vicent Moliner Journal of Chemical Information and Modeling 2021 61 (7), 3604-3614 DOI: 10.1021/acs.jcim.1c00425 | ca_CA |
dc.identifier.issn | 1549-9596 | |
dc.identifier.issn | 1549-960X | |
dc.identifier.uri | http://hdl.handle.net/10234/194941 | |
dc.description.abstract | Environmentally friendly processes are nowadays a trending topic to get highly desired chemical compounds and, in this sense, the use of enzyme-catalyzed routes is becoming a promising alternative to traditional synthetic methods. In the present paper, a hybrid quantum mechanics/molecular mechanics (QM/MM) computational study on the epoxidation of alkenes catalyzed by the Ser105Ala variant of the promiscuous Candida antarctica lipase B (CALB) is presented in an attempt to search for alternative paths to get useful intermediates in industries. The catalyzed reaction, described at the atomistic level with a model of the full solvated in a box of water molecules, is compared with the alternative epoxidation of alkenes by peroxy acids in chloroform. Free-energy profiles obtained at the density functional theory (DFT)/MM level show how Ser105Ala CALB is capable of epoxide short alkenes in a two-step process with free-energy barriers, in agreement with available experimental data, that are significantly lower than those of the single-step reaction in solution. The possible (R)-enantioselectivity dictated by the binding step, explored by means of alchemical QM/MM free-energy perturbation (FEP) methods, and the preference for the (S)-enantiomer derived from the free-energy landscape of the chemical steps would cancel out, thus predicting the lack of enantioselectivity experimentally observed. In general, our results provide general information on the molecular mechanism employed by a highly promiscuous enzyme, with potential applications in biotechnology. | ca_CA |
dc.format.extent | 38 p. | ca_CA |
dc.format.mimetype | application/pdf | ca_CA |
dc.language.iso | eng | ca_CA |
dc.publisher | American Chemical Society | ca_CA |
dc.relation.isPartOf | J. Chem. Inf. Model. 2021, 61, 3604−3614 | ca_CA |
dc.relation.uri | https://pubs.acs.org/doi/10.1021/acs.jcim.1c00425 | ca_CA |
dc.rights | © 2021 American Chemical Society | ca_CA |
dc.rights.uri | http://rightsstatements.org/vocab/InC/1.0/ | ca_CA |
dc.subject | hydrocarbons | ca_CA |
dc.subject | oxides | ca_CA |
dc.subject | peptides and proteins | ca_CA |
dc.subject | organic reactions | ca_CA |
dc.subject | chemical reactions | ca_CA |
dc.title | Computational Studies Suggest Promiscuous Candida antarctica Lipase B as an Environmentally Friendly Alternative for the Production of Epoxides | ca_CA |
dc.type | info:eu-repo/semantics/article | ca_CA |
dc.identifier.doi | https://doi.org/10.1021/acs.jcim.1c00425 | |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | ca_CA |
dc.relation.publisherVersion | https://pubs.acs.org/journal/jcisd8 | ca_CA |
dc.type.version | info:eu-repo/semantics/acceptedVersion | ca_CA |
project.funder.name | Ministerio de Ciencia e Innovación | ca_CA |
project.funder.name | Generalitat Valenciana | ca_CA |
project.funder.name | Universitat Jaume I | ca_CA |
oaire.awardNumber | PGC2018-094852-B-C21 | ca_CA |
oaire.awardNumber | PID2019-107098RJ-I00 | ca_CA |
oaire.awardNumber | AICO/2019/195 | ca_CA |
oaire.awardNumber | SEJI/2020/007 | ca_CA |
oaire.awardNumber | UJI-B2017-31 | ca_CA |
oaire.awardNumber | UJI-A2019-04 | ca_CA |
oaire.awardNumber | PREDOC/2017/23 | ca_CA |
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