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 Research
2013
Combined Lewis acid and Brønsted acid-mediated reactivity of glycosyl trichloroacetimidate donors
Gould ND, Allen C, Nam BC, Schepartz A, Miller SJ. Combined Lewis acid and Brønsted acid-mediated reactivity of glycosyl trichloroacetimidate donors. Carbohydrate Research 2013, 382: 36-42. PMID: 24177201, DOI: 10.1016/j.carres.2013.09.011.Peer-Reviewed Original ResearchConceptsLewis acidGlycosylation reactionsCombined Lewis acidControl reactionsSubsequent kinetic studiesCatalytic systemBiomimetic conditionsCarboxylic acidsGlycosyl donorsIrreversible reactionKinetic studiesReactionAcid actsCatalytic componentAcidActive enzymeCarbohydrate-active enzymesCatalystProof of principleReactivityDonorsGlycosylStructureAn efficient chemical synthesis of carboxylate-isostere analogs of daptomycin
Yoganathan S, Yin N, He Y, Mesleh MF, Gu YG, Miller SJ. An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin. Organic & Biomolecular Chemistry 2013, 11: 4680-4685. PMID: 23752953, PMCID: PMC4033608, DOI: 10.1039/c3ob40924d.Peer-Reviewed Original ResearchConceptsSide-chain carboxylic acid groupsDirect synthetic procedureEfficient chemical synthesisCarboxylic acid groupsCarboxylic acid moietySynthetic procedureChemical synthesisBackbone cyclizationEsterification protocolAcid groupsAcid moietyCarboxylate isosteresBackbone amidesSynthesisAspartic acidGlutamic acidAcidMoietyAnaloguesCyclizationEfficient methodIsosteresAmidesHerein
2011
Chemoenzymatic Synthesis of Each Enantiomer of Orthogonally Protected 4,4-Difluoroglutamic Acid: A Candidate Monomer for Chiral Brønsted Acid Peptide-Based Catalysts
Li Y, Miller SJ. Chemoenzymatic Synthesis of Each Enantiomer of Orthogonally Protected 4,4-Difluoroglutamic Acid: A Candidate Monomer for Chiral Brønsted Acid Peptide-Based Catalysts. The Journal Of Organic Chemistry 2011, 76: 9785-9791. PMID: 22039908, PMCID: PMC3228520, DOI: 10.1021/jo2018679.Peer-Reviewed Original ResearchConceptsDifluoroglutamic acidEnhanced catalytic activityFunctional group manipulationsΑ-amino acidGlutamic acid derivativesReduction reactionOxidation reactionParent amino acidCoupling reactionCatalytic activityCandidate monomersChemoenzymatic synthesisSelective formationAsymmetric synthesisGroup manipulationsScalable procedurePeptide bondEnzymatic resolutionAcid derivativesSynthetic materialsSynthesisReactionEnantiomersAcidCatalyst