2024
Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides
Huth S, Tampellini N, Guerrero M, Miller S. Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides. Organic Letters 2024, 26: 6872-6877. PMID: 39102356, PMCID: PMC11329351, DOI: 10.1021/acs.orglett.4c02452.Peer-Reviewed Original ResearchMeSH KeywordsAspartic AcidCatalysisHydrogen BondingMolecular StructureOxidation-ReductionPeptidesStereoisomerismSulfidesSulfoxidesConceptsEnantioselective oxidation of sulfidesModel of transition stateLevels of enantioinductionOxidation of sulfidesChiral sulfoxidesPeptide catalystsTransition stateEnantioselective sulfoxidationAspartic acid-containing peptidesSulfoxideThioethersEnantioinductionCatalystMoietySubstrateHydrogenSulfideExperimental evidence
2018
Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3‑Amidocyclohexanones
Shugrue C, Featherston AL, Lackner RM, Lin A, Miller SJ. Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3‑Amidocyclohexanones. The Journal Of Organic Chemistry 2018, 83: 4491-4504. PMID: 29547285, PMCID: PMC5963540, DOI: 10.1021/acs.joc.8b00207.Peer-Reviewed Original ResearchMeSH KeywordsAminationBiological ProductsCatalysisCyclohexanonesKineticsMolecular StructureOxidation-ReductionPhosphothreonineQuantum TheoryStereoisomerismConceptsReductive aminationNumerous reactive sitesPeptide catalystsParallel kinetic resolutionDFT calculationsNMR studiesReactive sitesDivergent selectivitySecondary interactionsNatural productsKinetic resolutionCatalystAminationDivergent stereoselectivitiesCatalyzed Reductive AminationPeptide sequencesSelectivityComplex substratesSubstrateDiastereoselectivityStereoselectivityProductsReactivityPhosphopeptidesPhosphothreonine
2017
Stereodynamic Quinone–Hydroquinone Molecules That Enantiomerize at sp3‑Carbon via Redox-Interconversion
Kim B, Storch G, Banerjee G, Mercado BQ, Castillo-Lora J, Brudvig GW, Mayer JM, Miller SJ. Stereodynamic Quinone–Hydroquinone Molecules That Enantiomerize at sp3‑Carbon via Redox-Interconversion. Journal Of The American Chemical Society 2017, 139: 15239-15244. PMID: 28931280, PMCID: PMC5735348, DOI: 10.1021/jacs.7b09176.Peer-Reviewed Original ResearchConceptsRedox-active substituentsStereogenic carbon atomCarbon-bearing moleculesFunctional group migrationRedox interconversionChiral compoundsOrganic moleculesMolecular chiralityDifferent substituentsHydroquinone groupsSp3 carbonCarbon centerEnantiomerization pathwayMaterials scienceCarbon atomsChemical processesConstituent bondsGroup migrationMoleculesDeracemization processSubstituentsBondsChiralityCompoundsEnantiomerization
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 ResearchMeSH KeywordsCatalysisCyclohexanonesMolecular StructureOxidation-ReductionPeptidesSolutionsStereoisomerismConceptsBaeyer-Villiger oxidationPeptide-based catalystsStereoselective Baeyer–Villiger oxidationsCatalytic reactionStereoselective catalystsEffect of additivesSolution conformationCatalystMolecular associationSubstrate-specific interactionsUnique structureSolution structureOxidationStructural analysisAdvantageous featuresSelectivityExperimental observationsPeptidesConformationStructureAdditivesReactionSynthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis
Featherston AL, Miller SJ. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis. Bioorganic & Medicinal Chemistry 2016, 24: 4871-4874. PMID: 27452284, PMCID: PMC5053897, DOI: 10.1016/j.bmc.2016.07.012.Peer-Reviewed Original ResearchMeSH KeywordsCatalysisCrystallography, X-RayEpoxy CompoundsKetonesModels, MolecularMolecular StructureOxidation-ReductionPeptidesPhenylalanine
2015
Site-Selective Reactions with Peptide-Based Catalysts
Giuliano MW, Miller SJ. Site-Selective Reactions with Peptide-Based Catalysts. 2015, 372: 157-201. PMID: 26307403, DOI: 10.1007/128_2015_653.Peer-Reviewed Original ResearchMeSH KeywordsCatalysisErythromycinGlycopeptidesMacrolidesOxidation-ReductionPeptidesPhosphorylationPyrones
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 ResearchMeSH KeywordsCatalysisKetonesKineticsOxidation-ReductionPeptidesStereoisomerismSubstrate SpecificityConceptsBaeyer-Villiger oxidationPeptide-based catalystsHydrogen bonding interactionsTypes of selectivityParallel kinetic resolutionCatalyst controlFunctionalized KetonesCyclic ketonesFunctional groupsNatural productsComplex moleculesKinetic resolutionAsymmetric processEnantioselectivityRegioKetonesOxidationBroad utilityCatalystCatalysisSelectivityAmidesSynthesisMoleculesProductsTotal synthesis and isolation of citrinalin and cyclopiamine congeners
Mercado-Marin EV, Garcia-Reynaga P, Romminger S, Pimenta EF, Romney DK, Lodewyk MW, Williams DE, Andersen RJ, Miller SJ, Tantillo DJ, Berlinck RG, Sarpong R. Total synthesis and isolation of citrinalin and cyclopiamine congeners. Nature 2014, 509: 318-324. PMID: 24828190, PMCID: PMC4117207, DOI: 10.1038/nature13273.Peer-Reviewed Original ResearchConceptsNitrogen atomsChemical synthesisMultiple nitrogen atomsBasic nitrogen atomTotal synthesisFunctional groupsNatural productsSelective introductionTarget moleculesSuch compoundsChemical connectionsSynthesisAtomsBiogenetic precursorBasicityCompoundsMoleculesBroad rangePrecursorsAlkaloidsPresenceCongenersProducts
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