2016
Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity
Alford JS, Abascal NC, Shugrue CR, Colvin SM, Romney DK, Miller SJ. Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity. ACS Central Science 2016, 2: 733-739. PMID: 27800556, PMCID: PMC5084076, DOI: 10.1021/acscentsci.6b00237.Peer-Reviewed Original ResearchBaeyer-Villiger oxidationAlkene epoxidationSmall-molecule catalystsModes of reactivityOrthogonal chemical reactivityFunctional group selectivityCarboxylic acid groupsCatalytic functional groupsLate-stage diversificationDifferent chemical reactionsActive site carboxylatesMacromolecular architecturesPolyfunctional moleculesChemical reactivityChemical selectivityElectrophilic oxidantSelective reactionGroup selectivityAmide bondAcid groupsFunctional groupsActive siteCatalytic mechanismChemical reactionsCatalyst
2013
An 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