2024
Complexes of Iron(II), Cobalt(II), and Nickel(II) with DOTA-Tetraglycinate for pH and Temperature Imaging Using Hyperfine Shifts of an Amide Moiety
Mishra S, Zakaria A, Mihailovic J, Maritim S, Mercado B, Coman D, Hyder F. Complexes of Iron(II), Cobalt(II), and Nickel(II) with DOTA-Tetraglycinate for pH and Temperature Imaging Using Hyperfine Shifts of an Amide Moiety. Inorganic Chemistry 2024, 63: 22559-22571. PMID: 39533962, DOI: 10.1021/acs.inorgchem.4c04023.Peer-Reviewed Original ResearchParamagnetic complexesDivalent transition-metal ionsNitrogen donor atomsLanthanide metal ionsComplexes of iron(IITransition-metal ionsChemical exchange saturation transferDonor atomsAmide moietyCrystallographic dataCoordination numberHyperfine shiftsMetal ionsPH sensitivityMoietyProtonIonsLow cytotoxicityPH imagingSaturation transferMagnetic resonanceCobalt(IINickel(IIIron(IILanthanideCatalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides
Huth S, Tampellini N, Guerrero M, Miller S. Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides. Organic Letters 2024, 26: 6872-6877. PMID: 39102356, PMCID: PMC11329351, DOI: 10.1021/acs.orglett.4c02452.Peer-Reviewed Original ResearchConceptsEnantioselective oxidation of sulfidesModel of transition stateLevels of enantioinductionOxidation of sulfidesChiral sulfoxidesPeptide catalystsTransition stateEnantioselective sulfoxidationAspartic acid-containing peptidesSulfoxideThioethersEnantioinductionCatalystMoietySubstrateHydrogenSulfideExperimental evidenceMtb-Selective 5‑Aminomethyl Oxazolidinone Prodrugs: Robust Potency and Potential Liabilities
Boshoff H, Young K, Ahn Y, Yadav V, Crowley B, Yang L, Su J, Oh S, Arora K, Andrews J, Manikkam M, Sutphin M, Smith A, Weiner D, Piazza M, Fleegle J, Gomez F, Dayao E, Prideaux B, Zimmerman M, Kaya F, Sarathy J, Tan V, Via L, Tschirret-Guth R, Lenaerts A, Robertson G, Dartois V, Olsen D, Barry C. Mtb-Selective 5‑Aminomethyl Oxazolidinone Prodrugs: Robust Potency and Potential Liabilities. ACS Infectious Diseases 2024, 10: 1679-1695. PMID: 38581700, DOI: 10.1021/acsinfecdis.4c00025.Peer-Reviewed Original ResearchConceptsLinezolid-resistant mutantsDrug-resistant patientsAntitubercular activityN-acetyl metaboliteOxazolidinone prodrugMechanism of actionC3HeB/FeJ miceAntimycobacterial activityN-acetyl transferaseSusceptible to inhibitionCross-resistanceOxazolidinoneCompoundsMoleculesMammalian metabolismN-acetyltransferaseProdrugToxicityMoietyProtein synthesisLinezolidC3HeB/FeJCaseumPatientsLiving cellsMass Spectrometry-Compatible Elution Technique Enables an Improved Mucin-Selective Enrichment Strategy to Probe the Mucinome
Mahoney K, Chang V, Lucas T, Maruszko K, Malaker S. Mass Spectrometry-Compatible Elution Technique Enables an Improved Mucin-Selective Enrichment Strategy to Probe the Mucinome. Analytical Chemistry 2024, 96: 5242-5250. PMID: 38512228, PMCID: PMC12050071, DOI: 10.1021/acs.analchem.3c05762.Peer-Reviewed Original ResearchMucin-domain glycoproteinsO-glycopeptidesGlycopeptide signalsIn-gel digestionMass spectrometryElution conditionsSolid supportBinding moietyElution stepDownstream analysisO-glycosylationIn-gelBiological functionsElutionHuman serumEnrichment strategyCell linesMoietyEffective isolationSpectrometryCatalyticallyGlycoproteinSampling requirementsGlycopeptidesStcEPolyMatch: Novel Libraries, Algorithms, and Visualizations for Discovering Polymers and Chemical Series
Koelmel J, Stelben P, Oranzi N, Kummer M, Godri D, Qi J, Rennie E, Lin E, Weil D, Pollitt K. PolyMatch: Novel Libraries, Algorithms, and Visualizations for Discovering Polymers and Chemical Series. Journal Of The American Society For Mass Spectrometry 2024, 35: 413-420. PMID: 38301121, DOI: 10.1021/jasms.3c00313.Peer-Reviewed Original ResearchAccurate mass matchingChemical moietiesQ-TOF instrumentMS/MS libraryPolymer databaseSeries polymersEsterified speciesLC-HRMS/MSHomologous seriesMass matchingFunctional groupsRepeat unitsAdvancement of materials sciencePolyethylene glycolContaining fragmentsMaterials scienceMoietyDegree of unsaturationPolymerPhysicochemical propertiesChemical speciesFragment coverageHTML linksIterative exclusionMolecular level
2021
Chemoselective restoration of para-azido-phenylalanine at multiple sites in proteins
Arranz-Gibert P, Vanderschuren K, Haimovich A, Halder A, Gupta K, Rinehart J, Isaacs FJ. Chemoselective restoration of para-azido-phenylalanine at multiple sites in proteins. Cell Chemical Biology 2021, 29: 1046-1052.e4. PMID: 34965380, PMCID: PMC10173106, DOI: 10.1016/j.chembiol.2021.12.002.Peer-Reviewed Original ResearchConceptsProtein functionalizationChemical moietiesDiverse chemical moietiesDiverse chemical groupsSite-specific incorporationClick reactionOff-target modificationsDiazotransfer reactionAzide moietyAzide reductionNonstandard amino acidsChemical groupsFunctionalizationMaterials scienceMoietyPAZFFunction of proteinsReactionAzideBroad applicationsPhysiological conditionsParaChemistryAmino acidsKey limitations
2019
Itaconyl-CoA forms a stable biradical in methylmalonyl-CoA mutase and derails its activity and repair
Ruetz M, Campanello GC, Purchal M, Shen H, McDevitt L, Gouda H, Wakabayashi S, Zhu J, Rubin EJ, Warncke K, Mootha VK, Koutmos M, Banerjee R. Itaconyl-CoA forms a stable biradical in methylmalonyl-CoA mutase and derails its activity and repair. Science 2019, 366: 589-593. PMID: 31672889, PMCID: PMC7070230, DOI: 10.1126/science.aay0934.Peer-Reviewed Original ResearchMeSH KeywordsBiocatalysisCatalytic DomainCoenzyme ACrystallography, X-RayDeoxyadenosinesElectron Spin Resonance SpectroscopyHumansHydrogen BondingMacrophagesMethylmalonyl-CoA MutaseModels, MolecularMycobacterium tuberculosisPropionatesProtein ConformationProtein MultimerizationProtein SubunitsSuccinatesVitamin B 12N,N,O Pincer Ligand with a Deprotonatable Site That Promotes Redox‐Leveling, High Mn Oxidation States, and a Mn2O2 Dimer Competent for Catalytic Oxygen Evolution
Lant H, Michaelos T, Sharninghausen L, Mercado B, Crabtree R, Brudvig G. N,N,O Pincer Ligand with a Deprotonatable Site That Promotes Redox‐Leveling, High Mn Oxidation States, and a Mn2O2 Dimer Competent for Catalytic Oxygen Evolution. European Journal Of Inorganic Chemistry 2019, 2019: 2115-2123. DOI: 10.1002/ejic.201801343.Peer-Reviewed Original ResearchAlkoxide moietyOxidation stateOxygen evolutionHigher Mn oxidation statesCatalytic oxygen evolutionO-pincer ligandMn oxidation statePincer ligandRedox levelingElectrochemical dataLow overpotentialProtonation stateProton lossEPR experimentsMn IIIO intermediateRelated seriesMn–VMn IIMoietyLigandsOverpotentialDicationCatalystCatalysis
2018
Greener Methodology: An Aldol Condensation of an Unprotected C‑Glycoside with Solid Base Catalysts
de Winter T, Petitjean L, Erythropel H, Moreau M, Hitce J, Coish P, Zimmerman J, Anastas P. Greener Methodology: An Aldol Condensation of an Unprotected C‑Glycoside with Solid Base Catalysts. ACS Sustainable Chemistry & Engineering 2018, 6: 7810-7817. DOI: 10.1021/acssuschemeng.8b00816.Peer-Reviewed Original ResearchSolid base catalystBase catalystC-glycosidesElectron-poor moietiesAldol condensation reactionMultiple reaction parametersCatalytic systemCondensation reactionMgO catalystReaction conditionsExcellent yieldsAromatic aldehydesAldol condensationBulky groupsReaction parametersGreen alternativeCatalystOptimal conditionsRecyclabilityMoietyAldehydesKetonesSynthesisReactionCondensation
2016
Synthesis and in Vitro and in Vivo Evaluation of MMP-12 Selective Optical Probes
Bordenave T, Helle M, Beau F, Georgiadis D, Tepshi L, Bernes M, Ye Y, Levenez L, Poquet E, Nozach H, Razavian M, Toczek J, Stura EA, Dive V, Sadeghi MM, Devel L. Synthesis and in Vitro and in Vivo Evaluation of MMP-12 Selective Optical Probes. Bioconjugate Chemistry 2016, 27: 2407-2417. PMID: 27564088, PMCID: PMC5100701, DOI: 10.1021/acs.bioconjchem.6b00377.Peer-Reviewed Original ResearchConceptsDye moietyLinker lengthSelective optical probeVivo performanceDye structureFirst crystal structureCyanine dyesHydrophilic characterSeries of tracersSelective probeReporter groupCrystal structureNovel seriesBlood clearance rateFluorescent probePseudopeptide inhibitorsWhole conjugateNet chargeMoietyCrystallographic structureSelectivity profileSmall peptidesOptical probeVivo behaviorVivo evaluationSite‐Specific In Vivo Bioorthogonal Ligation via Chemical Modulation
Koo H, Lee J, Bao K, Wu Y, Fakhri G, Henary M, Yun S, Choi H. Site‐Specific In Vivo Bioorthogonal Ligation via Chemical Modulation. Advanced Healthcare Materials 2016, 5: 2510-2516. PMID: 27568818, PMCID: PMC5541365, DOI: 10.1002/adhm.201600574.Peer-Reviewed Original ResearchConceptsClick chemistryClick moietyEfficiency of click chemistryLow reaction efficiencyIn vivo click chemistryReaction efficiencyChemical structureBioorthogonal ligationMoietyChemistryBioorthogonal click chemistryNear-infrared fluorophoreChemical modulatorsSurface chargeTetrazinePharmacokinetic barriersLipophilicityControlled pharmacokineticsFluorophores
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 strategyA2-2ComplexesSynthesis of 11β-ether-17α-ethinyl-3,17β-estradiols with strong ER antagonist activities
Zhang J, Labaree D, Hochberg R. Synthesis of 11β-ether-17α-ethinyl-3,17β-estradiols with strong ER antagonist activities. Chinese Chemical Letters 2014, 25: 567-570. DOI: 10.1016/j.cclet.2014.01.015.Peer-Reviewed Original ResearchExperimental Lineage and Functional Analysis of a Remotely Directed Peptide Epoxidation Catalyst
Lichtor PA, Miller SJ. Experimental Lineage and Functional Analysis of a Remotely Directed Peptide Epoxidation Catalyst. Journal Of The American Chemical Society 2014, 136: 5301-5308. PMID: 24690108, PMCID: PMC4333582, DOI: 10.1021/ja410567a.Peer-Reviewed Original Research
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 functionalityCatalysisMoietySpectroscopyAn 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
Covalent Attachment of a Rhenium Bipyridyl CO2 Reduction Catalyst to Rutile TiO2
Anfuso C, Snoeberger R, Ricks A, Liu W, Xiao D, Batista V, Lian T. Covalent Attachment of a Rhenium Bipyridyl CO2 Reduction Catalyst to Rutile TiO2. Journal Of The American Chemical Society 2011, 133: 6922-6925. PMID: 21504161, DOI: 10.1021/ja2013664.Peer-Reviewed Original ResearchSum frequency generation spectroscopyCO2 reduction catalystsDensity functional theory calculationsFrequency generation spectroscopyFunctional theory calculationsReduction catalystCarboxylate groupsGeneration spectroscopyTheory calculationsCovalent attachmentLinkage motifsCovalent bindingCatalystCatalysisMoietySpectroscopySurfaceTiO2ComplexesCharacterization of Short-Lived Electrophilic Metabolites of the Anticancer Agent Laromustine (VNP40101M)
Nassar A, King I, Du J. Characterization of Short-Lived Electrophilic Metabolites of the Anticancer Agent Laromustine (VNP40101M). Chemical Research In Toxicology 2011, 24: 568-578. PMID: 21361357, DOI: 10.1021/tx100453t.Peer-Reviewed Original ResearchConceptsHuman liver microsomesNuclear magnetic resonance spectroscopyPhase II conjugatesN-acetylecysteinePooled human liver microsomesFragment ionsLiver microsomesPhase 1 metabolismCofactor nicotinamide adenine dinucleotide phosphateReactive intermediatesMoietyElectrophilic metabolitesMagnetic resonance spectroscopyM-4MethylformamidePhysiological pHVNP40101MResonance spectroscopyLaromustineConjugateActive moietyRearrangementAlkylating agentsH-DCysteine
2008
One-Pot Tandem Decarboxylative Allylation−Heck Cyclization of Allyl Diphenylglycinate Imines: Rapid Access to Polyfunctionalized 1-Aminoindanes
Fields W, Khan A, Sabat M, Chruma J. One-Pot Tandem Decarboxylative Allylation−Heck Cyclization of Allyl Diphenylglycinate Imines: Rapid Access to Polyfunctionalized 1-Aminoindanes. Organic Letters 2008, 10: 5131-5134. PMID: 18956870, DOI: 10.1021/ol801986m.Peer-Reviewed Original ResearchAsymmetric Synthesis of (−)-Incarvillateine Employing an Intramolecular Alkylation via Rh-Catalyzed Olefinic C−H Bond Activation
Tsai AS, Bergman RG, Ellman JA. Asymmetric Synthesis of (−)-Incarvillateine Employing an Intramolecular Alkylation via Rh-Catalyzed Olefinic C−H Bond Activation. Journal Of The American Chemical Society 2008, 130: 6316-6317. PMID: 18444613, PMCID: PMC2713182, DOI: 10.1021/ja8012159.Peer-Reviewed Original Research
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