2024
Scaffold‐Oriented Asymmetric Catalysis: Conformational Modulation of Transition State Multivalency during a Catalyst‐Controlled Assembly of a Pharmaceutically Relevant Atropisomer
Tampellini N, Mercado B, Miller S. Scaffold‐Oriented Asymmetric Catalysis: Conformational Modulation of Transition State Multivalency during a Catalyst‐Controlled Assembly of a Pharmaceutically Relevant Atropisomer. Chemistry - A European Journal 2024, 30: e202401109. PMID: 38507249, PMCID: PMC11132932, DOI: 10.1002/chem.202401109.Peer-Reviewed Original ResearchHydrogen bond donorAtroposelective synthesisAsymmetric catalysisGuanidine catalystCatalyst controlChiral axisBond donorNoncovalent interactionsConformational modulationCatalystFolded stateN-capAtroposelectivityAtropisomersSuperbasesPhenylCatalysisQuinazolinedionesMultivalencyBTK inhibitorsMechanistic frameworkStructure
2018
Disulfide-Bridged Peptides That Mediate Enantioselective Cycloadditions through Thiyl Radical Catalysis
Ryss JM, Turek AK, Miller SJ. Disulfide-Bridged Peptides That Mediate Enantioselective Cycloadditions through Thiyl Radical Catalysis. Organic Letters 2018, 20: 1621-1625. PMID: 29504763, PMCID: PMC5963541, DOI: 10.1021/acs.orglett.8b00364.Peer-Reviewed Original Research
2017
Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis
Toste FD, Sigman MS, Miller SJ. Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis. Accounts Of Chemical Research 2017, 50: 609-615. PMID: 28945415, PMCID: PMC5643260, DOI: 10.1021/acs.accounts.6b00613.Peer-Reviewed Original Research
2016
Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis
Featherston AL, Miller SJ. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis. Bioorganic & Medicinal Chemistry 2016, 24: 4871-4874. PMID: 27452284, PMCID: PMC5053897, DOI: 10.1016/j.bmc.2016.07.012.Peer-Reviewed Original ResearchDistal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling
Kim B, Chinn AJ, Fandrick DR, Senanayake CH, Singer RA, Miller SJ. Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling. Journal Of The American Chemical Society 2016, 138: 7939-7945. PMID: 27254785, PMCID: PMC5127171, DOI: 10.1021/jacs.6b03444.Peer-Reviewed Original Research
2015
Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle
Melicher MS, Walker AS, Shen J, Miller SJ, Schepartz A. Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle. Organic Letters 2015, 17: 4718-4721. PMID: 26376076, DOI: 10.1021/acs.orglett.5b02187.Peer-Reviewed Original ResearchStructure 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
Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones
Romney DK, Colvin SM, Miller SJ. Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones. Journal Of The American Chemical Society 2014, 136: 14019-14022. PMID: 25250713, PMCID: PMC4195385, DOI: 10.1021/ja508757g.Peer-Reviewed Original ResearchConceptsBaeyer-Villiger oxidationPeptide-based catalystsHydrogen bonding interactionsTypes of selectivityParallel kinetic resolutionCatalyst controlFunctionalized KetonesCyclic ketonesFunctional groupsNatural productsComplex moleculesKinetic resolutionAsymmetric processEnantioselectivityRegioKetonesOxidationBroad utilityCatalystCatalysisSelectivityAmidesSynthesisMoleculesProducts
2013
A Fully Synthetic and Biochemically Validated Phosphatidyl Inositol-3-Phosphate Hapten via Asymmetric Synthesis and Native Chemical Ligation
Chandler BD, Burkhardt AL, Foley K, Cullis C, Driscoll D, D’Amore N, Miller SJ. A Fully Synthetic and Biochemically Validated Phosphatidyl Inositol-3-Phosphate Hapten via Asymmetric Synthesis and Native Chemical Ligation. Journal Of The American Chemical Society 2013, 136: 412-418. PMID: 24344932, PMCID: PMC3919123, DOI: 10.1021/ja410750a.Peer-Reviewed Original ResearchAsymmetric Catalysis at a Distance: Catalytic, Site-Selective Phosphorylation of Teicoplanin
Han S, Miller SJ. Asymmetric Catalysis at a Distance: Catalytic, Site-Selective Phosphorylation of Teicoplanin. Journal Of The American Chemical Society 2013, 135: 12414-12421. PMID: 23924210, PMCID: PMC3790668, DOI: 10.1021/ja406067v.Peer-Reviewed Original ResearchConceptsTeicoplanin A2-2Site-selective phosphorylationPeptide-based catalystsSmall-molecule catalystsX-ray crystal structureCatalyst-substrate interactionsSet of catalystsDistinct hydroxyl groupsAsymmetric catalysisCatalytic controlStructural assignmentCatalystTeicoplanin derivativesNatural productsGlycopeptide structuresHydroxyl groupsCrystal structureMass spectrometryMechanistic studiesBiological activityCatalytic moietyAdditional functionalityCatalysisMoietySpectroscopy
2011
Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities
Dermenci A, Selig PS, Domaoal RA, Spasov KA, Anderson KS, Miller SJ. Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities. Chemical Science 2011, 2: 1568-1572. PMID: 24179673, PMCID: PMC3811095, DOI: 10.1039/c1sc00221j.Peer-Reviewed Original Research