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Tetrahydropyran-based dipeptides as asymmetric catalysts for a 1,4-addition reaction
Jorge Borges‐González, Andrés Feher Voelger, Fernando R. Pinacho Crisóstomo, Tomás Martı́n
Bibliographic record
VenueDIGITAL.CSIC (Spanish National Research Council (CSIC)) · 2016
Typearticle
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicChemical Synthesis and Analysis
Canadian institutionsnot available
FundersArmy Research LaboratoryEuropean Social FundDivision of ChemistryBerrikuntza + Ikerketa + Osasuna Eusko FundazioaInstituto Superior TécnicoInstituto de Salud Carlos IIIConsejo Superior de Investigaciones CientíficasAgència de Gestió d'Ajuts Universitaris i de RecercaScience and Technology Facilities CouncilAlliance for Accelerating Excellence in Science in AfricaNatural Environment Research CouncilNatural Sciences and Engineering Research Council of CanadaMultidisciplinary University Research InitiativeOffice of ScienceNational Oceanic and Atmospheric AdministrationNational Institutes of HealthMinisterio para la Transición Ecológica y el Reto DemográficoGrifolsInstituto Español de OceanografíaEngineering and Physical Sciences Research CouncilElectricité de FranceJunta de Castilla y LeónFundación Domingo MartínezFundació Barcelona ZooFondo Nacional de Desarrollo Científico y TecnológicoJunta de Comunidades de Castilla-La ManchaJunta de AndalucíaXunta de GaliciaConsejo Nacional de Ciencia, Tecnología e Innovación TecnológicaDirección General de Investigación Científica y TécnicaUniversitas LampungMinisterio de Asuntos Económicos y Transformación Digital, Gobierno de EspañaFP7 Food, Agriculture and Fisheries, BiotechnologyMedizinische Universität GrazRegione PugliaPontificia Universidad Católica de ChileFundación Juan MarchTechnische Universität MünchenKarl-Franzens-Universität GrazFundación para el Fomento en Asturias de la Investigación Científica Aplicada y la TecnologíaInstituto de Ciencias MatemáticasJoint Genome InstituteMinistry of DefenseMinisterio de Agricultura y Pesca, Alimentación y Medio AmbienteUniversidad Pública de NavarraAgencia Estatal de InvestigaciónFundación Sandra Ibarra de Solidaridad Frente al CáncerUniversidade Federal de Juiz de ForaJapan Society for the Promotion of ScienceCoordenação de Aperfeiçoamento de Pessoal de Nível SuperiorComisión de Operación y Fomento de Actividades Académicas, Instituto Politécnico NacionalUniversity of Cape TownUniversidad de ZaragozaEuskal Herriko UnibertsitateaInstitut National de la Recherche AgronomiqueBarcelona Supercomputing CenterCYTED Ciencia y Tecnología para el DesarrolloCentro de Investigación Biomédica en Red en Bioingeniería, Biomateriales y NanomedicinaUniversidad de Las Palmas de Gran CanariaCentro de Ciências do MarDeutsche ForschungsgemeinschaftUniversidad Carlos III de MadridMinistério da Ciência, Tecnologia e Ensino SuperiorUniversidade de LisboaHorizon 2020 Framework ProgrammeUniversität HamburgCentre National de la Recherche ScientifiqueUniversidad de Buenos AiresInstituto Madrileño de Investigación y Desarrollo Rural, Agrario y AlimentarioFundação de Amparo à Pesquisa do Estado de Minas GeraisUniversitat de BarcelonaUniversity of TehranSecretaría de Ciencia y Técnica, Universidad de Buenos AiresUniversidade de CoimbraLawrence Berkeley National LaboratoryEuropean Regional Development FundKU LeuvenMinistry of EnvironmentUniversitat de les Illes BalearsUniversitat de ValènciaMinistero della transizione ecologicaMinisterio de Economía y CompetitividadConsejo Nacional de Ciencia y TecnologíaBanco Bilbao Vizcaya ArgentariaFundação para a Ciência e a TecnologiaEuropean Association of National Metrology InstitutesMinistarstvo Prosvete, Nauke i Tehnološkog RazvojaMinisterio de Educación, Cultura y DeporteUniversitat Autònoma de BarcelonaMcGill UniversityGeneralitat de CatalunyaMinisterio de Ciencia e InnovaciónFundación SénecaDirectorate for Biological SciencesEusko JaurlaritzaUniversitat Politècnica de CatalunyaUniversidad de HuelvaConsejo Nacional de Investigaciones Científicas y TécnicasInstituto Tecnológico y de Estudios Superiores de MonterreyFP7 People: Marie-Curie ActionsGobierno de AragónInstitut Català de Nanociència i NanotecnologiaCentre National d’Etudes SpatialesEidgenössische Technische Hochschule ZürichAgentúra na Podporu Výskumu a VývojaGeneralitat ValencianaUniversity of OxfordBranco Weiss Fellowship – Society in ScienceUniversity of California, San DiegoConselho Nacional de Desenvolvimento Científico e TecnológicoCentro para el Desarrollo Tecnológico IndustrialEuropean CommissionFundação de Amparo à Pesquisa do Estado de São PauloInstituto Dom Luiz, Universidade de LisboaCurtin University of TechnologyUniversity of BathEuropean Space AgencyCentro de Biología Molecular Severo OchoaAgence Nationale de la RechercheFundación BBVAFundación BiodiversidadAustralian GovernmentGreat Lakes Bioenergy Research CenterHelsingin YliopistoCentres de Recerca de CatalunyaPetrobrasDirecció General de Recerca, Generalitat de CatalunyaInstitute of Materials Science and Engineering, Washington University in St. LouisFundación Ramón ArecesRégion NormandieSwiss Polar InstituteStrongNational Institute of Diabetes and Digestive and Kidney DiseasesRoyal SocietyGrenoble École de ManagementUniversiteit StellenboschUniversidad Complutense de MadridNational Institute of Allergy and Infectious DiseasesITEAAbdus Salam International Centre for Theoretical PhysicsComunidad de MadridStatens Serum InstitutIrish Research CouncilInterregU.S. Department of AgricultureSpanish National Plan for Scientific and Technical Research and InnovationUniversidad Autónoma de MadridNational Science FoundationFundación General CSICCiência sem FronteirasUniversité de BordeauxOrganismo Autónomo de Parques NacionalesU.S. Department of EnergyBureau de Recherches Géologiques et MinièresInstituto Nacional de Investigación y Tecnología Agraria y AlimentariaUniversidad de Castilla-La ManchaMinisterio de Ciencia, Innovación y UniversidadesErasmus+Centro de Estudos Ambientais e Marinhos, Universidade de AveiroUS-UK Fulbright CommissionBasic Energy SciencesUniversidad de Alicante
KeywordsTetrahydropyranCatalysisChemistryPhilosophyOrganic chemistry
Abstract
Amino transaminases (ATAs) have been supported on a 2D ITQ-2 zeolite through electrostatic interactions, resulting in a highly stable active biocatalyst to obtain a variety of valuable chiral amines starting from prochiral ketones derived from biomass. We have extended the biocatalyst applications by designing a chemo-enzymatic process that allows, as the first step, prochiral ketones to be obtained from biomass-derived compounds through an aldol condensation–reduction step using a bifunctional metal/base catalyst. The prochiral ketone is subsequently converted into the chiral amine using the immobilized ATA. We show that it is feasible to couple both steps in a semi-continuous process to produce industrially relevant chiral amines with yields of >95% and ∼100% enantiomer excess.
Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.
How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
metaresearch head score (Codex)0.003
metaresearch head score (Gemma)0.039
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMetaresearch
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: none
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.438
Threshold uncertainty score0.970
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.003 | 0.039 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
Opus teacher head0.097
GPT teacher head0.339
Teacher spread0.241 · how far apart the two teachers sit on this one work
Validation status
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
Study designBench or experimental
Domainnot available
GenreEmpirical
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".
Quick stats
Citations12
Published2016
Admission routes1
Has abstractyes