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
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 ResearchConceptsTeicoplanin 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 functionalityCatalysisMoietySpectroscopy