2024
Disulfide Tethering to Map Small Molecule Binding Sites Transcriptome-wide
Moon M, Vock I, Streit A, Connor L, Senkina J, Ellman J, Simon M. Disulfide Tethering to Map Small Molecule Binding Sites Transcriptome-wide. ACS Chemical Biology 2024, 19: 2081-2086. PMID: 39192734, PMCID: PMC11683664, DOI: 10.1021/acschembio.4c00538.Peer-Reviewed Original ResearchCytochrome c oxidase 1Binding sitesRNA-small molecule interactionsPotential binding sitesTranscriptome-wide screeningSmall molecule disulfideSpinal muscular atrophyCellular RNARNA sitesTarget RNAMetabolic labelingSmall molecule bindingRNADisulfide analoguesLead moleculesMolecule bindingTranscriptomeFDA-approved drugsStructural probesMolecule interactionsCovalent attachmentDisulfide tetherThermodynamic propertiesTreat spinal muscular atrophyDisulfide
2003
Improved Synthesis of tert-Butanesulfinamide Suitable for Large-Scale Production
Weix DJ, Ellman JA. Improved Synthesis of tert-Butanesulfinamide Suitable for Large-Scale Production. Organic Letters 2003, 5: 1317-1320. PMID: 12688748, DOI: 10.1021/ol034254b.Peer-Reviewed Original ResearchCatalytic asymmetric oxidationHomogeneous reaction conditionsChiral ligandsAsymmetric oxidationImproved synthesisReaction conditionsDi-tertButyl disulfidePrevious synthesesSolvent acetoneLarge-scale productionSingle stepSynthesisKey stepM concentrationLigandsOxidationAcetoneDisulfideReactionStepMaterials
2002
Enantioselective Oxidation of Di-tert-Butyl Disulfide with a Vanadium Catalyst: Progress toward Mechanism Elucidation †
Blum SA, Bergman RG, Ellman JA. Enantioselective Oxidation of Di-tert-Butyl Disulfide with a Vanadium Catalyst: Progress toward Mechanism Elucidation †. The Journal Of Organic Chemistry 2002, 68: 150-155. PMID: 12515473, DOI: 10.1021/jo0205560.Peer-Reviewed Original ResearchSolvent effectsDi-tertChiral Schiff base ligandsButyl disulfideSchiff base ligandDramatic solvent effectVanadium catalystsNMR spectroscopyCatalyst precursorsEnantioselective oxidationReaction enantioselectivityOxidation pathwayMechanism elucidationEnantioselectivityFull characterizationLigandsOxidationDisulfideCatalystSpectroscopyThiosulfinatesReactionPrecursorsElucidationCharacterization
1998
Catalytic Asymmetric Oxidation of tert-Butyl Disulfide. Synthesis of tert-Butanesulfinamides, tert-Butyl Sulfoxides, and tert-Butanesulfinimines
Cogan D, Liu G, Kim K, Backes B, Ellman J. Catalytic Asymmetric Oxidation of tert-Butyl Disulfide. Synthesis of tert-Butanesulfinamides, tert-Butyl Sulfoxides, and tert-Butanesulfinimines. Journal Of The American Chemical Society 1998, 120: 8011-8019. DOI: 10.1021/ja9809206.Peer-Reviewed Original ResearchCatalytic asymmetric oxidationTert-butyl disulfideAsymmetric oxidationChiral Schiff base ligandsEster 2Schiff base ligandTert-butyl sulfoxidesBase ligandStoichiometric oxidantChiral sulfoxidesGrignard reagentsTert-butanesulfinamideExcellent precursorDisulfide 1Liquid ammoniaLithium amideNucleophilic displacementGood yieldsEnantiomeric excessOverall yieldFirst exampleSingle recrystallizationOxidationSulfoxideDisulfide
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