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 approach
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 principleReactivityDonorsGlycosylStructure