2015
A stepwise dechlorination/cross-coupling strategy to diversify the vancomycin ‘in-chloride’
Wadzinski TJ, Gea KD, Miller SJ. A stepwise dechlorination/cross-coupling strategy to diversify the vancomycin ‘in-chloride’. Bioorganic & Medicinal Chemistry Letters 2015, 26: 1025-1028. PMID: 26725950, PMCID: PMC4728044, DOI: 10.1016/j.bmcl.2015.12.027.Peer-Reviewed Original ResearchAnti-Bacterial AgentsBoronic AcidsCatalysisChloridesHalogenationMethicillin-Resistant Staphylococcus aureusMicrobial Sensitivity TestsStaphylococcus aureusVancomycinVancomycin ResistanceStructure 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 ResearchMeSH KeywordsAnti-Bacterial AgentsCatalysisCrystallography, X-RayEnterococcusGlycopeptidesLipidsLipoylationMethicillin-Resistant Staphylococcus aureusMicrobial Sensitivity TestsMolecular ConformationMolecular StructureStructure-Activity RelationshipVancomycinVancomycin ResistanceConceptsStructure diversificationLipid chain lengthStructure-activity relationship studiesPeptide catalystsCatalytic approachAliphatic hydroxylDerivatization sitesDerivatives 9aGlycopeptide-resistant pathogensNovel antibiotic leadsChain lengthLipid chainsRelationship studiesAntibiotic leadsCatalystCatalysisAntibiotic-resistant infectionsHydroxylHereinScaffoldsBioactivityChainSpectraLipidationIncorporation
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 ResearchMeSH KeywordsAnti-Bacterial AgentsCrystallography, X-RayDose-Response Relationship, DrugEnterococcusMethicillin-Resistant Staphylococcus aureusMicrobial Sensitivity TestsModels, MolecularMolecular ConformationStructure-Activity RelationshipTeicoplaninVancomycin ResistanceConceptsNew 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