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 ResearchConceptsReductive aminationNumerous reactive sitesPeptide catalystsParallel kinetic resolutionDFT calculationsNMR studiesReactive sitesDivergent selectivitySecondary interactionsNatural productsKinetic resolutionCatalystAminationDivergent stereoselectivitiesCatalyzed Reductive AminationPeptide sequencesSelectivityComplex substratesSubstrateDiastereoselectivityStereoselectivityProductsReactivityPhosphopeptidesPhosphothreonine
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 ResearchMeSH KeywordsCatalysisCrystallography, X-RayModels, MolecularPeptidesProtein ConformationQuantum TheoryConceptsPeptide-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