2016
Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity
Alford JS, Abascal NC, Shugrue CR, Colvin SM, Romney DK, Miller SJ. Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity. ACS Central Science 2016, 2: 733-739. PMID: 27800556, PMCID: PMC5084076, DOI: 10.1021/acscentsci.6b00237.Peer-Reviewed Original ResearchBaeyer-Villiger oxidationAlkene epoxidationSmall-molecule catalystsModes of reactivityOrthogonal chemical reactivityFunctional group selectivityCarboxylic acid groupsCatalytic functional groupsLate-stage diversificationDifferent chemical reactionsActive site carboxylatesMacromolecular architecturesPolyfunctional moleculesChemical reactivityChemical selectivityElectrophilic oxidantSelective reactionGroup selectivityAmide bondAcid groupsFunctional groupsActive siteCatalytic mechanismChemical reactionsCatalyst
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 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