2013
Chemical 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