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dc.contributor.authorSiebert, David C B
dc.contributor.authorSommer, Roman
dc.contributor.authorPogorevc, Domen
dc.contributor.authorHoffmann, Michael
dc.contributor.authorWenzel, Silke C
dc.contributor.authorMüller, Rolf
dc.contributor.authorTitz, Alexander
dc.date.accessioned2020-01-13T11:36:10Z
dc.date.available2020-01-13T11:36:10Z
dc.date.issued2019-01-01
dc.identifier.citationBeilstein J Org Chem. 2019 Dec 5;15:2922-2929. doi: 10.3762/bjoc.15.286. eCollection 2019.en_US
dc.identifier.issn1860-5397
dc.identifier.pmid31839838
dc.identifier.doi10.3762/bjoc.15.286
dc.identifier.urihttp://hdl.handle.net/10033/622075
dc.description.abstractThe argyrins are secondary metabolites from myxobacteria with antibiotic activity against Pseudomonas aeruginosa. Studying their structure-activity relationship is hampered by the complexity of the chemical total synthesis. Mutasynthesis is a promising approach where simpler and fully synthetic intermediates of the natural product's biosynthesis can be biotechnologically incorporated. Here, we report the synthesis of a series of tripeptide thioesters as mutasynthons containing the native sequence with a dehydroalanine (Dha) Michael acceptor attached to a sarcosine (Sar) and derivatives. Chemical synthesis of the native sequence ᴅ-Ala-Dha-Sar thioester required revision of the sequential peptide synthesis into a convergent strategy where the thioester with sarcosine was formed before coupling to the Dha-containing dipeptide.en_US
dc.language.isoenen_US
dc.publisherBeilstein Instituten_US
dc.rightsAttribution-NonCommercial-ShareAlike 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.subjectNRPSen_US
dc.subjectantibioticen_US
dc.subjectargyrinen_US
dc.subjectmutasynthesisen_US
dc.subjectpeptide synthesisen_US
dc.titleChemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis.en_US
dc.typeArticleen_US
dc.contributor.departmentBRICS, Braunschweiger Zentrum für Systembiologie, Rebenring 56,38106 Braunschweig, Germany.en_US
dc.identifier.journalBeilstein Journal of Organic Chemistryen_US
refterms.dateFOA2020-01-13T11:36:11Z
dc.source.journaltitleBeilstein journal of organic chemistry


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