2018
Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent
Wadzinski TJ, Steinauer A, Hie L, Pelletier G, Schepartz A, Miller SJ. Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent. Nature Chemistry 2018, 10: 644-652. PMID: 29713033, PMCID: PMC5964040, DOI: 10.1038/s41557-018-0041-8.Peer-Reviewed Original ResearchConceptsUnprotected peptidesSmall moleculesAmino acid functionalitiesHigh functional group toleranceFunctional group toleranceFree synthesisAcid functionalityProteinogenic amino acidsAqueous solventSelective formationSynthetic glycopeptidesAnomeric productsPhenolic functionalityGroup toleranceNatural productsGood yieldsSide chainsGlycosyl donorsBiochemical probesAryl glycosidesRoom temperatureMoleculesO-glycosylationPeptidesSimple approach
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
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 ResearchRegioselective Derivatizations of a Tribrominated Atropisomeric Benzamide Scaffold
Barrett KT, Miller SJ. Regioselective Derivatizations of a Tribrominated Atropisomeric Benzamide Scaffold. Organic Letters 2015, 17: 580-583. PMID: 25582814, PMCID: PMC4364386, DOI: 10.1021/ol503593y.Peer-Reviewed Original ResearchConceptsLithium-halogen exchangeAsymmetric ligandsBenzamide scaffoldChiral moleculesRegioselective derivatizationEnantioselective synthesisGroup installationRegioselective transformationSequential PdAllylic alkylationHigh regioselectivityMoleculesBenzamidesPhosphinoDerivatizationRegioselectivityAlkylationLigandsTribromideSynthesisDerivativesPdScaffoldsPotential utility
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
2013
Chiral Copper(II) Complex-Catalyzed Reactions of Partially Protected Carbohydrates
Allen CL, Miller SJ. Chiral Copper(II) Complex-Catalyzed Reactions of Partially Protected Carbohydrates. Organic Letters 2013, 15: 6178-6181. PMID: 24274325, DOI: 10.1021/ol4033072.Peer-Reviewed Original ResearchConceptsCoupling of electrophilesCarbohydrate chemistryDivergent regioselectivityRegioselective functionalizationCatalyzed reactionsSaccharide moleculesSuch reactionsCatalystReactionManipulation stepsFunctionalizationChemistryElectrophilesChiralRegioselectivityEnantiomersSynthesisMoleculesHereinCopperSugars
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