Biosynthetic plasticity enables production of fluorinated aurachins

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dc.contributor.authorSester, Angela
dc.contributor.authorStüer-Patowsky, Katrin
dc.contributor.authorHiller, Wolf
dc.contributor.authorKloss, Florian
dc.contributor.authorLütz, Stephan
dc.contributor.authorNett, Markus
dc.date.accessioned2021-07-29T08:16:22Z
dc.date.available2021-07-29T08:16:22Z
dc.date.issued2020-03-26
dc.description.abstractRoom for a halogen: The plasticity of the aurachin biosynthetic pathway in the myxobacterium S. erecta was explored for the use of fluoro- and chloroanthranilic acids. Incorporation of the unnatural precursors was quantified. Three fluorinated aurachin analogues were produced in sufficient quantity to enable their antibacterial activities to be assessed. Enzyme promiscuity has important implications in the field of biocatalysis. In some cases, structural analogues of simple metabolic building blocks can be processed through entire pathways to give natural product derivatives that are not readily accessible by chemical means. In this study, we explored the plasticity of the aurachin biosynthesis pathway with regard to using fluoro- and chloroanthranilic acids, which are not abundant in the bacterial producers of these quinolone antibiotics. The incorporation rates of the tested precursor molecules disclosed a regiopreference for halogen substitution as well as steric limitations of enzymatic substrate tolerance. Three previously undescribed fluorinated aurachin derivatives were produced in preparative amounts by fermentation and structurally characterized. Furthermore, their antibacterial activities were evaluated in comparison to their natural congener aurachin D.en
dc.identifier.urihttp://hdl.handle.net/2003/40349
dc.identifier.urihttp://dx.doi.org/10.17877/DE290R-22224
dc.language.isoende
dc.relation.ispartofseriesChemBioChem;Vol. 21. 2020, issue 16, pp 2268-2273
dc.subjectAurachinen
dc.subjectBiosynthesisen
dc.subjectBiotransformationen
dc.subjectMyxobacteriaen
dc.subjectStigmatellaen
dc.subject.ddc660
dc.subject.rswkGyrasehemmerde
dc.subject.rswkBiosynthesede
dc.subject.rswkBiotransformationde
dc.subject.rswkMyxobakteriende
dc.subject.rswkStigmatella aurantiacade
dc.titleBiosynthetic plasticity enables production of fluorinated aurachinsen
dc.typeTextde
dc.type.publicationtypearticlede
dcterms.accessRightsopen access
eldorado.secondarypublicationtruede
eldorado.secondarypublication.primarycitationChemBioChem. Vol. 21. 2020, issue 16, pp 2268-2273en
eldorado.secondarypublication.primaryidentifierhttps://doi.org/10.1002/cbic.202000166de

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