2016
Diversity of Secondary Structure in Catalytic Peptides with β‑Turn-Biased Sequences
Metrano AJ, Abascal NC, Mercado BQ, Paulson EK, Hurtley AE, Miller SJ. Diversity of Secondary Structure in Catalytic Peptides with β‑Turn-Biased Sequences. Journal Of The American Chemical Society 2016, 139: 492-516. PMID: 28029251, PMCID: PMC5312972, DOI: 10.1021/jacs.6b11348.Peer-Reviewed Original ResearchConceptsPeptide-based catalystsSolid-state structural featuresΒ-turn secondary structureX-ray crystal structureProton chemical shiftsCorresponding solution structuresSymmetry-independent moleculesX-ray crystallographyAccessible transition stateGround state conformationSeries of tetrapeptidesChemical shiftsDifferent peptide sequencesEnantioselective reactionsSecondary structureCatalytic activityBromination reactionSame unit cellCatalytic peptidesTransition stateCrystal structureCatalystState conformationComputational studyConformational equilibrium
2015
Enantioselective Synthesis of 3‑Arylquinazolin-4(3H)‑ones via Peptide-Catalyzed Atroposelective Bromination
Diener ME, Metrano AJ, Kusano S, Miller SJ. Enantioselective Synthesis of 3‑Arylquinazolin-4(3H)‑ones via Peptide-Catalyzed Atroposelective Bromination. Journal Of The American Chemical Society 2015, 137: 12369-12377. PMID: 26343278, PMCID: PMC5134330, DOI: 10.1021/jacs.5b07726.Peer-Reviewed Original ResearchConceptsAtroposelective brominationDensity functional theory calculationsBroad substrate scopeX-ray crystallographyΒ-turn peptideFunctional theory calculationsCross-coupling sequenceFree catalystsSubstrate scopeAmination procedureStereochemical informationEnantioselective synthesisTheory calculationsHigh enantioselectivityRotational barriersMechanistic studiesSubsequent transformationBrominationMono-orthoProduct of interestCatalystEnantioinductionCrystallographyEnantioselectivityIsomers