2017
Applications of Nonenzymatic Catalysts to the Alteration of Natural Products
Shugrue CR, Miller SJ. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products. Chemical Reviews 2017, 117: 11894-11951. PMID: 28580785, PMCID: PMC5742423, DOI: 10.1021/acs.chemrev.7b00022.Peer-Reviewed Original ResearchConceptsNatural productsNonenzymatic catalystsComplex molecular scaffoldsComplex natural productsH bond functionalizationC bond formationNatural product scaffoldsLate-stage functionalizationNatural product derivativesSynthesis of analoguesChemical functionalityMedicinal chemistryBond functionalizationElectrophilic reagentsOlefin functionalizationSelectivity challengesBiological activity assaysBond formationEnzymatic catalystsProduct derivativesMolecular scaffoldsCatalystComplex moleculesChemical remodelingSmall molecules
2015
Structure Diversification of Vancomycin through Peptide-Catalyzed, Site-Selective Lipidation: A Catalysis-Based Approach To Combat Glycopeptide-Resistant Pathogens
Yoganathan S, Miller SJ. Structure Diversification of Vancomycin through Peptide-Catalyzed, Site-Selective Lipidation: A Catalysis-Based Approach To Combat Glycopeptide-Resistant Pathogens. Journal Of Medicinal Chemistry 2015, 58: 2367-2377. PMID: 25671771, PMCID: PMC4364393, DOI: 10.1021/jm501872s.Peer-Reviewed Original ResearchConceptsStructure diversificationLipid chain lengthStructure-activity relationship studiesPeptide catalystsCatalytic approachAliphatic hydroxylDerivatization sitesDerivatives 9aGlycopeptide-resistant pathogensNovel antibiotic leadsChain lengthLipid chainsRelationship studiesAntibiotic leadsCatalystCatalysisAntibiotic-resistant infectionsHydroxylHereinScaffoldsBioactivityChainSpectraLipidationIncorporation
2014
X‑ray Crystal Structure of Teicoplanin A2‑2 Bound to a Catalytic Peptide Sequence via the Carrier Protein Strategy
Han S, Le BV, Hajare HS, Baxter RH, Miller SJ. X‑ray Crystal Structure of Teicoplanin A2‑2 Bound to a Catalytic Peptide Sequence via the Carrier Protein Strategy. The Journal Of Organic Chemistry 2014, 79: 8550-8556. PMID: 25147913, PMCID: PMC4168787, DOI: 10.1021/jo501625f.Peer-Reviewed Original ResearchConceptsX-ray crystal structureTeicoplanin A2-2Crystal structurePeptide-based catalystsProtein ligation (IPL) techniqueCatalyst moietyPeptide catalystsComplex crystal structureMolecular arrangementN-methylimidazoleNucleophilic nitrogenObserved selectivitySugar ringCatalystPeptide sequencesT4 lysozymeDerivativesN-acetylglucosaminePhosphorylation reactionMoietyStructureSelectivityProtein strategyA2-2Complexes
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 stepsFunctionalizationChemistryElectrophilesChiralRegioselectivityEnantiomersSynthesisMoleculesHereinCopperSugarsChemical 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