2018
Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3‑Arylquinazolin-4(3H)‑ones
Crawford JM, Stone EA, Metrano AJ, Miller SJ, Sigman MS. Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3‑Arylquinazolin-4(3H)‑ones. Journal Of The American Chemical Society 2018, 140: 868-871. PMID: 29300461, PMCID: PMC5817992, DOI: 10.1021/jacs.7b11303.Peer-Reviewed Original ResearchMeSH KeywordsCatalysisHalogenationModels, MolecularPeptidesProtein Conformation, beta-StrandQuinazolinonesStereoisomerism
2017
Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst
Hurtley AE, Stone EA, Metrano AJ, Miller SJ. Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst. The Journal Of Organic Chemistry 2017, 82: 11326-11336. PMID: 29020446, PMCID: PMC5738245, DOI: 10.1021/acs.joc.7b02339.Peer-Reviewed Original ResearchMeSH KeywordsCatalysisCrystallography, X-RayHalogenationKineticsModels, MolecularMolecular StructurePeptidesPhenolsStereoisomerism
2016
Diversity of Secondary Structure in Catalytic Peptides with β‑Turn-Biased Sequences
Metrano AJ, Abascal NC, Mercado BQ, Paulson EK, Hurtley AE, Miller SJ. Diversity of Secondary Structure in Catalytic Peptides with β‑Turn-Biased Sequences. Journal Of The American Chemical Society 2016, 139: 492-516. PMID: 28029251, PMCID: PMC5312972, DOI: 10.1021/jacs.6b11348.Peer-Reviewed Original ResearchMeSH KeywordsCatalysisCrystallography, X-RayModels, MolecularPeptidesProtein ConformationQuantum TheoryConceptsPeptide-based catalystsSolid-state structural featuresΒ-turn secondary structureX-ray crystal structureProton chemical shiftsCorresponding solution structuresSymmetry-independent moleculesX-ray crystallographyAccessible transition stateGround state conformationSeries of tetrapeptidesChemical shiftsDifferent peptide sequencesEnantioselective reactionsSecondary structureCatalytic activityBromination reactionSame unit cellCatalytic peptidesTransition stateCrystal structureCatalystState conformationComputational studyConformational equilibriumSynthesis 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
2013
Asymmetric Catalysis at a Distance: Catalytic, Site-Selective Phosphorylation of Teicoplanin
Han S, Miller SJ. Asymmetric Catalysis at a Distance: Catalytic, Site-Selective Phosphorylation of Teicoplanin. Journal Of The American Chemical Society 2013, 135: 12414-12421. PMID: 23924210, PMCID: PMC3790668, DOI: 10.1021/ja406067v.Peer-Reviewed Original ResearchMeSH KeywordsAcetylglucosamineBinding SitesBiocatalysisMannoseModels, MolecularPeptidomimeticsPhosphorylationProtein ConformationTeicoplaninConceptsTeicoplanin A2-2Site-selective phosphorylationPeptide-based catalystsSmall-molecule catalystsX-ray crystal structureCatalyst-substrate interactionsSet of catalystsDistinct hydroxyl groupsAsymmetric catalysisCatalytic controlStructural assignmentCatalystTeicoplanin derivativesNatural productsGlycopeptide structuresHydroxyl groupsCrystal structureMass spectrometryMechanistic studiesBiological activityCatalytic moietyAdditional functionalityCatalysisMoietySpectroscopyChemical Tailoring of Teicoplanin with Site-Selective Reactions
Pathak TP, Miller SJ. Chemical Tailoring of Teicoplanin with Site-Selective Reactions. Journal Of The American Chemical Society 2013, 135: 8415-8422. PMID: 23692563, PMCID: PMC3800266, DOI: 10.1021/ja4038998.Peer-Reviewed Original ResearchConceptsNew compoundsSelective cross-coupling reactionsChemical reactionsOrthogonal chemical reactionsSite-selective reactionsTotal chemical synthesisCross-coupling reactionsNatural product derivativesTwo-step accessChemical tailoringChemical synthesisProduct derivativesChemical modificationPoor selectivityAntibacterial propertiesAntibiotic teicoplaninReactionChemical alterationImproved analoguesCompoundsUnmet challengeAnaloguesSelectivitySemisynthesisComplex structure
2012
Catalytic Site-Selective Thiocarbonylations and Deoxygenations of Vancomycin Reveal Hydroxyl-Dependent Conformational Effects
Fowler BS, Laemmerhold KM, Miller SJ. Catalytic Site-Selective Thiocarbonylations and Deoxygenations of Vancomycin Reveal Hydroxyl-Dependent Conformational Effects. Journal Of The American Chemical Society 2012, 134: 9755-9761. PMID: 22621706, PMCID: PMC3374881, DOI: 10.1021/ja302692j.Peer-Reviewed Original ResearchConceptsPeptide-based catalystsForm of vancomycinNew compoundsVancomycin derivativesRational designConformational consequencesCatalystConformational effectsNew analoguesSelectivity profileBiological activityThiocarbonylationDeoxygenationNative structureStructural roleHydroxylCompoundsDerivativesAnaloguesSubstrateStructure