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
2015
Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle
Melicher MS, Walker AS, Shen J, Miller SJ, Schepartz A. Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle. Organic Letters 2015, 17: 4718-4721. PMID: 26376076, DOI: 10.1021/acs.orglett.5b02187.Peer-Reviewed Original Research
2013
The Roles of Counterion and Water in a Stereoselective Cysteine‐Catalyzed Rauhut–Currier Reaction: A Challenge for Computational Chemistry
Osuna S, Dermenci A, Miller SJ, Houk KN. The Roles of Counterion and Water in a Stereoselective Cysteine‐Catalyzed Rauhut–Currier Reaction: A Challenge for Computational Chemistry. Chemistry - A European Journal 2013, 19: 14245-14253. PMID: 24038400, PMCID: PMC3918516, DOI: 10.1002/chem.201300745.Peer-Reviewed Original ResearchConceptsRauhut-Currier reactionCysteine derivativesComplete reaction pathwayRole of counterionsPresence of counterionsRate-determining eliminationMichael addition productsDensity functional theoryComputational chemistryExplicit water solvationWater solvationPotassium counterionsReaction conditionsReaction pathwaysAddition productsEnantiomer pairsThiol catalystCatalyst eliminationPossible stereoisomersCurrier ReactionFunctional theoryCounterionsNucleophilesReactionDerivatives