2016
Solution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer–Villiger Oxidation
Abascal NC, Miller SJ. Solution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer–Villiger Oxidation. Organic Letters 2016, 18: 4646-4649. PMID: 27588823, PMCID: PMC5130343, DOI: 10.1021/acs.orglett.6b02282.Peer-Reviewed Original ResearchConceptsBaeyer-Villiger oxidationPeptide-based catalystsStereoselective Baeyer–Villiger oxidationsCatalytic reactionStereoselective catalystsEffect of additivesSolution conformationCatalystMolecular associationSubstrate-specific interactionsUnique structureSolution structureOxidationStructural analysisAdvantageous featuresSelectivityExperimental observationsPeptidesConformationStructureAdditivesReaction
2015
A Synergistic Combinatorial and Chiroptical Study of Peptide Catalysts for Asymmetric Baeyer–Villiger Oxidation
Giuliano MW, Lin C, Romney DK, Miller SJ, Anslyn EV. A Synergistic Combinatorial and Chiroptical Study of Peptide Catalysts for Asymmetric Baeyer–Villiger Oxidation. Advanced Synthesis & Catalysis 2015, 357: 2301-2309. PMID: 26543444, PMCID: PMC4629862, DOI: 10.1002/adsc.201500230.Peer-Reviewed Original ResearchAsymmetric Baeyer–Villiger oxidationBaeyer-Villiger oxidationSolution-phase reactionsBaeyer-Villiger monooxygenasesPeptide catalystsCatalyst discoveryChiroptical studiesSpeed of analysisCatalyst performanceFocused libraryLactone productsAsymmetric inductionAbsolute configurationCombinatorial screeningOxidationCatalystDistinct parallelsProductsReactionHPLCAlcoholMonooxygenases
2014
Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones
Romney DK, Colvin SM, Miller SJ. Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones. Journal Of The American Chemical Society 2014, 136: 14019-14022. PMID: 25250713, PMCID: PMC4195385, DOI: 10.1021/ja508757g.Peer-Reviewed Original ResearchConceptsBaeyer-Villiger oxidationPeptide-based catalystsHydrogen bonding interactionsTypes of selectivityParallel kinetic resolutionCatalyst controlFunctionalized KetonesCyclic ketonesFunctional groupsNatural productsComplex moleculesKinetic resolutionAsymmetric processEnantioselectivityRegioKetonesOxidationBroad utilityCatalystCatalysisSelectivityAmidesSynthesisMoleculesProducts
2012
Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation
Lichtor PA, Miller SJ. Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation. Nature Chemistry 2012, 4: 990-995. PMID: 23174978, PMCID: PMC3506257, DOI: 10.1038/nchem.1469.Peer-Reviewed Original ResearchConceptsPeptide-based catalystsPossible stereochemical outcomesNon-enzymatic catalystsSimilar functional groupsCatalytic functionalizationEnantioselective catalystsChemical synthesisCombinatorial synthesisOxidation catalystAsymmetric oxidationEnzymatic catalysisCatalystEnantioselective oxidationFunctional groupsComplex moleculesStereochemical outcomeEvolution of enzymesSame moleculeOxidationSelectivitySynthesisCombinatorial evolutionMoleculesExhibit siteOnly precedent