2014
X‑ray Crystal Structure of Teicoplanin A2‑2 Bound to a Catalytic Peptide Sequence via the Carrier Protein Strategy
Han S, Le BV, Hajare HS, Baxter RH, Miller SJ. X‑ray Crystal Structure of Teicoplanin A2‑2 Bound to a Catalytic Peptide Sequence via the Carrier Protein Strategy. The Journal Of Organic Chemistry 2014, 79: 8550-8556. PMID: 25147913, PMCID: PMC4168787, DOI: 10.1021/jo501625f.Peer-Reviewed Original ResearchConceptsX-ray crystal structureTeicoplanin A2-2Crystal structurePeptide-based catalystsProtein ligation (IPL) techniqueCatalyst moietyPeptide catalystsComplex crystal structureMolecular arrangementN-methylimidazoleNucleophilic nitrogenObserved selectivitySugar ringCatalystPeptide sequencesT4 lysozymeDerivativesN-acetylglucosaminePhosphorylation reactionMoietyStructureSelectivityProtein strategyA2-2Complexes
2013
Asymmetric Catalysis at a Distance: Catalytic, Site-Selective Phosphorylation of Teicoplanin
Han S, Miller SJ. Asymmetric Catalysis at a Distance: Catalytic, Site-Selective Phosphorylation of Teicoplanin. Journal Of The American Chemical Society 2013, 135: 12414-12421. PMID: 23924210, PMCID: PMC3790668, DOI: 10.1021/ja406067v.Peer-Reviewed Original ResearchConceptsTeicoplanin A2-2Site-selective phosphorylationPeptide-based catalystsSmall-molecule catalystsX-ray crystal structureCatalyst-substrate interactionsSet of catalystsDistinct hydroxyl groupsAsymmetric catalysisCatalytic controlStructural assignmentCatalystTeicoplanin derivativesNatural productsGlycopeptide structuresHydroxyl groupsCrystal structureMass spectrometryMechanistic studiesBiological activityCatalytic moietyAdditional functionalityCatalysisMoietySpectroscopyChemical Tailoring of Teicoplanin with Site-Selective Reactions
Pathak TP, Miller SJ. Chemical Tailoring of Teicoplanin with Site-Selective Reactions. Journal Of The American Chemical Society 2013, 135: 8415-8422. PMID: 23692563, PMCID: PMC3800266, DOI: 10.1021/ja4038998.Peer-Reviewed Original ResearchConceptsNew compoundsSelective cross-coupling reactionsChemical reactionsOrthogonal chemical reactionsSite-selective reactionsTotal chemical synthesisCross-coupling reactionsNatural product derivativesTwo-step accessChemical tailoringChemical synthesisProduct derivativesChemical modificationPoor selectivityAntibacterial propertiesAntibiotic teicoplaninReactionChemical alterationImproved analoguesCompoundsUnmet challengeAnaloguesSelectivitySemisynthesisComplex structure