2018
Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3‑Amidocyclohexanones
Shugrue C, Featherston AL, Lackner RM, Lin A, Miller SJ. Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3‑Amidocyclohexanones. The Journal Of Organic Chemistry 2018, 83: 4491-4504. PMID: 29547285, PMCID: PMC5963540, DOI: 10.1021/acs.joc.8b00207.Peer-Reviewed Original ResearchMeSH KeywordsAminationBiological ProductsCatalysisCyclohexanonesKineticsMolecular StructureOxidation-ReductionPhosphothreonineQuantum TheoryStereoisomerismConceptsReductive aminationNumerous reactive sitesPeptide catalystsParallel kinetic resolutionDFT calculationsNMR studiesReactive sitesDivergent selectivitySecondary interactionsNatural productsKinetic resolutionCatalystAminationDivergent stereoselectivitiesCatalyzed Reductive AminationPeptide sequencesSelectivityComplex substratesSubstrateDiastereoselectivityStereoselectivityProductsReactivityPhosphopeptidesPhosphothreonine
2017
Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids
Key HM, Miller SJ. Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids. Journal Of The American Chemical Society 2017, 139: 15460-15466. PMID: 28975793, PMCID: PMC5736372, DOI: 10.1021/jacs.7b08775.Peer-Reviewed Original ResearchMeSH KeywordsAmino AcidsAnti-Bacterial AgentsBiological ProductsCatalysisMicrobial Sensitivity TestsRhodiumThiostreptonConceptsComplex moleculesSite-selective catalysisComplex molecular settingsComplex natural productsSite-selective modificationPotassium saltNew analoguesApplication of RhFunctional group toleranceEnantioselective catalysisSelective functionalizationCatalyst systemAnalogous reactionStereoselective functionalizationEnantioselective synthesisGroup toleranceNatural productsActive moleculesPotent antibacterial propertiesDehydroalanine residuesBiological testingAmino estersHigh stereoselectivityAntibacterial propertiesMolecular settingApplications 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
2014
Total synthesis and isolation of citrinalin and cyclopiamine congeners
Mercado-Marin EV, Garcia-Reynaga P, Romminger S, Pimenta EF, Romney DK, Lodewyk MW, Williams DE, Andersen RJ, Miller SJ, Tantillo DJ, Berlinck RG, Sarpong R. Total synthesis and isolation of citrinalin and cyclopiamine congeners. Nature 2014, 509: 318-324. PMID: 24828190, PMCID: PMC4117207, DOI: 10.1038/nature13273.Peer-Reviewed Original ResearchConceptsNitrogen atomsChemical synthesisMultiple nitrogen atomsBasic nitrogen atomTotal synthesisFunctional groupsNatural productsSelective introductionTarget moleculesSuch compoundsChemical connectionsSynthesisAtomsBiogenetic precursorBasicityCompoundsMoleculesBroad rangePrecursorsAlkaloidsPresenceCongenersProducts