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MATEO: intermolecular α-amidoalkylation theoretical enantioselectivity optimization. Online tool for selection and design of chiral catalysts and products
dc.contributor.author | Carracedo-Reboredo, Paula | |
dc.contributor.author | Aranzamendi, Eider | |
dc.contributor.author | He, Shan | |
dc.contributor.author | Arrasate, Sonia | |
dc.contributor.author | Munteanu, Cristian-Robert | |
dc.contributor.author | Fernández-Lozano, Carlos | |
dc.contributor.author | Sotomayor, Nuria | |
dc.contributor.author | Lete, Esther | |
dc.contributor.author | González-Díaz, Humberto | |
dc.date.accessioned | 2024-04-23T07:03:41Z | |
dc.date.available | 2024-04-23T07:03:41Z | |
dc.date.issued | 2024-01-23 | |
dc.identifier.citation | Carracedo-Reboredo, P., Aranzamendi, E., He, S. et al. MATEO: intermolecular α-amidoalkylation theoretical enantioselectivity optimization. Online tool for selection and design of chiral catalysts and products. J Cheminform 16, 9 (2024). https://doi.org/10.1186/s13321-024-00802-7 | es_ES |
dc.identifier.issn | 1758-2946 | |
dc.identifier.uri | http://hdl.handle.net/2183/36302 | |
dc.description.abstract | [Absctract]: The enantioselective Brønsted acid-catalyzed α-amidoalkylation reaction is a useful procedure is for the production of new drugs and natural products. In this context, Chiral Phosphoric Acid (CPA) catalysts are versatile catalysts for this type of reactions. The selection and design of new CPA catalysts for different enantioselective reactions has a dual interest because new CPA catalysts (tools) and chiral drugs or materials (products) can be obtained. However, this process is difficult and time consuming if approached from an experimental trial and error perspective. In this work, an Heuristic Perturbation-Theory and Machine Learning (HPTML) algorithm was used to seek a predictive model for CPA catalysts performance in terms of enantioselectivity in α-amidoalkylation reactions with R2 = 0.96 overall for training and validation series. It involved a Monte Carlo sampling of > 100,000 pairs of query and reference reactions. In addition, the computational and experimental investigation of a new set of intermolecular α-amidoalkylation reactions using BINOL-derived N-triflylphosphoramides as CPA catalysts is reported as a case of study. The model was implemented in a web server called MATEO: InterMolecular Amidoalkylation Theoretical Enantioselectivity Optimization, available online at: https://cptmltool.rnasa-imedir.com/CPTMLTools-Web/mateo. This new user-friendly online computational tool would enable sustainable optimization of reaction conditions that could lead to the design of new CPA catalysts along with new organic synthesis products. | es_ES |
dc.description.sponsorship | The authors acknowledge financial support from Grant PID2019-104148 GB-I00 and PID2022-137365NB-I00 funded by MCIN/ AEI/10.13039/501100011033 and Grant IT1558-22 funded by Basque Government/Eusko Jaurlaritza, 2022–2025.CITIC is funded by the Xunta de Galicia through the collaboration agreement between the Department of Culture, Education, Vocational Training and Universities and the Galician universities to strengthen the research centers of the Galician University System (CIGUS). | es_ES |
dc.description.sponsorship | Eusko Jaurlaritza; IT1558-22 | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | BMC | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-104148GB-I00/ES/NUEVAS HERRAMIENTAS SINTETICAS Y QUIMIOINFORMATICAS PARA LA CONSTRUCCION Y DIVERSIFICACION DE HETEROCICLOS ¿DRUG-LIKE¿. ACTIVACION C-H Y MACHINE LEARNING | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-137365NB-I00/ES/ESTRATEGIAS PARA LA ACTIVACION C-H CATALIZADA POR METALES-3D. APLICACIONES SINTETICAS Y APRENDIZAJE AUTOMATICO EN ESTUDIOS DE REACTIVIDAD QUIMICA Y ACTIVIDAD BIOLOGICA | es_ES |
dc.relation.uri | https://doi.org/10.1186/s13321-024-00802-7 | es_ES |
dc.rights | Atribución 3.0 España | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/es/ | * |
dc.subject | Chiral phosphoric acid catalysts | es_ES |
dc.subject | Cheminformatics | es_ES |
dc.subject | Machine learning | es_ES |
dc.subject | Amidoalkylation | es_ES |
dc.title | MATEO: intermolecular α-amidoalkylation theoretical enantioselectivity optimization. Online tool for selection and design of chiral catalysts and products | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.access | info:eu-repo/semantics/openAccess | es_ES |
UDC.journalTitle | Journal of Cheminformatics | es_ES |
UDC.volume | 16 | es_ES |
UDC.startPage | 9 | es_ES |
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