Thiol-ene Enabled Chemical Synthesis of Truncated S | teixobactin

ThisarticleispartoftheResearchTopicWomeninScience:ChemistryViewall42ArticlesArticlesXuechenLITheUniversityofHongKong,HongKong,SARChinaElisabethLojouFR3479InstitutdeMicrobiologiedelaMéditerranée(IMM),FranceLakshminarayananRajamaniSingaporeEyeResearchInstitute(SERI),SingaporeTheeditorandreviewers'affiliationsarethelatestprovidedontheirLoopresearchprofilesandmaynotreflecttheirsituationatthetimeofreview.AbstractIntroductionResultsandDiscussionConclusionsDataAvailabilityStatementAuthorContributionsFundingConflictofInterestSupplementaryMaterialReferencesSuggestaResearchTopic>DownloadArticleDownloadPDFReadCubeEPUBXML(NLM)SupplementaryMaterialExportcitationEndNoteReferenceManagerSimpleTEXTfileBibTextotalviewsViewArticleImpactSuggestaResearchTopic>SHAREONOpenSupplementalDataORIGINALRESEARCHarticleFront.Chem.,04August2020|https://doi.org/10.3389/fchem.2020.00568Thiol-eneEnabledChemicalSynthesisofTruncatedS-LipidatedTeixobactinAnalogsVictorV.Yim1,2,AlanJ.Cameron1,2,3,ImanKavianinia1,2,3,PaulW.R.Harris1,2,3*andMargaretA.Brimble1,2,3*1SchoolofBiologicalSciences,UniversityofAuckland,Auckland,NewZealand2SchoolofChemicalSciences,UniversityofAuckland,Auckland,NewZealand3MauriceWilkinsCentreforMolecularBiodiscovery,UniversityofAuckland,Auckland,NewZealandHereinisdescribedtheintroductionoflipidmoietiesontoasimplifiedteixobactinpharmacophoreusingamodifiedCysteineLipidationonaPeptideorAminoacid(CLipPA)technique,wherebycysteinewassubstitutedfor3-mercaptopropionicacid(3-MPA).Atruncatedteixobactinanalogwaspreparedwiththerequisitethiolhandle,thusenablinganarrayofvinylesterstobeconvenientlyconjugatedontothesimplifiedteixobactinpharmacophoretoyieldS-lipidatedcycliclipopeptides.IntroductionNaturehashistoricallybeentheprimarysourceofmedicinallyimportantantibiotics(Moloney,2016).Byscreeningsoilmicroorganisms,Lingetal.discoveredthenovelantimicrobialpeptide(AMP)teixobactin(1,Figure1),isolatedfrombacteriumEleftheriaterrae(Lingetal.,2015).TeixobactinexhibitedpotentactivityagainstGram-positivepathoge


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