2018
Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent
Wadzinski TJ, Steinauer A, Hie L, Pelletier G, Schepartz A, Miller SJ. Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent. Nature Chemistry 2018, 10: 644-652. PMID: 29713033, PMCID: PMC5964040, DOI: 10.1038/s41557-018-0041-8.Peer-Reviewed Original ResearchConceptsUnprotected peptidesSmall moleculesAmino acid functionalitiesHigh functional group toleranceFunctional group toleranceFree synthesisAcid functionalityProteinogenic amino acidsAqueous solventSelective formationSynthetic glycopeptidesAnomeric productsPhenolic functionalityGroup toleranceNatural productsGood yieldsSide chainsGlycosyl donorsBiochemical probesAryl glycosidesRoom temperatureMoleculesO-glycosylationPeptidesSimple approachDisulfide-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 ResearchParameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3‑Arylquinazolin-4(3H)‑ones
Crawford JM, Stone EA, Metrano AJ, Miller SJ, Sigman MS. Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3‑Arylquinazolin-4(3H)‑ones. Journal Of The American Chemical Society 2018, 140: 868-871. PMID: 29300461, PMCID: PMC5817992, DOI: 10.1021/jacs.7b11303.Peer-Reviewed Original Research
2017
A bottom up approach towards artificial oxygenases by combining iron coordination complexes and peptides
Cussó O, Giuliano MW, Ribas X, Miller SJ, Costas M. A bottom up approach towards artificial oxygenases by combining iron coordination complexes and peptides. Chemical Science 2017, 8: 3660-3667. PMID: 29270284, PMCID: PMC5734052, DOI: 10.1039/c7sc00099e.Peer-Reviewed Original ResearchIron centerHigh enantioselectivityIron coordination complexesAqueous hydrogen peroxideSecond coordination sphereΒ-turn structureShort reaction timesTerminal carboxylic acidSupramolecular catalystsCoordination complexesSupramolecular systemsClasses of substratesAsymmetric catalysisCoordination sphereAsymmetric epoxidationExcellent yieldsCarboxylic acidsCombination of peptidesActivation stepHydrogen peroxideReaction timeEpoxidationEnantioselectivityPeptidesCatalyst
2016
Solution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer–Villiger Oxidation
Abascal NC, Miller SJ. Solution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer–Villiger Oxidation. Organic Letters 2016, 18: 4646-4649. PMID: 27588823, PMCID: PMC5130343, DOI: 10.1021/acs.orglett.6b02282.Peer-Reviewed Original ResearchConceptsBaeyer-Villiger oxidationPeptide-based catalystsStereoselective Baeyer–Villiger oxidationsCatalytic reactionStereoselective catalystsEffect of additivesSolution conformationCatalystMolecular associationSubstrate-specific interactionsUnique structureSolution structureOxidationStructural analysisAdvantageous featuresSelectivityExperimental observationsPeptidesConformationStructureAdditivesReactionSynthesis 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
Site-Selective Reactions with Peptide-Based Catalysts
Giuliano MW, Miller SJ. Site-Selective Reactions with Peptide-Based Catalysts. 2015, 372: 157-201. PMID: 26307403, DOI: 10.1007/128_2015_653.Peer-Reviewed Original ResearchPhosphothreonine as a Catalytic Residue in Peptide‐Mediated Asymmetric Transfer Hydrogenations of 8‐Aminoquinolines
Shugrue CR, Miller SJ. Phosphothreonine as a Catalytic Residue in Peptide‐Mediated Asymmetric Transfer Hydrogenations of 8‐Aminoquinolines. Angewandte Chemie International Edition 2015, 54: 11173-11176. PMID: 26246129, PMCID: PMC4628550, DOI: 10.1002/anie.201505898.Peer-Reviewed Original ResearchConceptsTransfer hydrogenationChiral phosphoric acid catalystHydrogen bonding interactionsPhosphoric acid catalystAsymmetric transfer hydrogenationEnantioselective transfer hydrogenationAsymmetric catalystsAcid catalystStrong complexationNMR studiesSubstrate classesCatalystHydrogenationNew classCatalytic residuesPeptidesComplexationEnantioselectivityQuinolinePhosphopeptidesSubstrateResidues
2014
Diastereo- and Enantioselective Addition of Anilide-Functionalized Allenoates to N‑Acylimines Catalyzed by a Pyridylalanine-Based Peptide
Mbofana CT, Miller SJ. Diastereo- and Enantioselective Addition of Anilide-Functionalized Allenoates to N‑Acylimines Catalyzed by a Pyridylalanine-Based Peptide. Journal Of The American Chemical Society 2014, 136: 3285-3292. PMID: 24527787, DOI: 10.1021/ja412996f.Peer-Reviewed Original Research