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dc.contributor.authorPreisitsch, Michael
dc.contributor.authorHeiden, Stefan E
dc.contributor.authorBeerbaum, Monika
dc.contributor.authorNiedermeyer, Timo H J
dc.contributor.authorSchneefeld, Marie
dc.contributor.authorHerrmann, Jennifer
dc.contributor.authorKumpfmüller, Jana
dc.contributor.authorThürmer, Andrea
dc.contributor.authorNeidhardt, Inga
dc.contributor.authorWiesner, Christoph
dc.contributor.authorDaniel, Rolf
dc.contributor.authorMüller, Rolf
dc.contributor.authorBange, Franz-Christoph
dc.contributor.authorSchmieder, Peter
dc.contributor.authorSchweder, Thomas
dc.contributor.authorMundt, Sabine
dc.date.accessioned2016-03-17T15:33:33Zen
dc.date.available2016-03-17T15:33:33Zen
dc.date.issued2016en
dc.identifier.citationEffects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2. 2016, 14 (1): Mar Drugsen
dc.identifier.issn1660-3397en
dc.identifier.pmid26805858en
dc.identifier.doi10.3390/md14010021en
dc.identifier.urihttp://hdl.handle.net/10033/602094en
dc.description.abstractIn this study, the influence of halide ions on [7.7]paracyclophane biosynthesis in the cyanobacterium Nostoc sp. CAVN2 was investigated. In contrast to KI and KF, supplementation of the culture medium with KCl or KBr resulted not only in an increase of growth but also in an up-regulation of carbamidocyclophane production. LC-MS analysis indicated the presence of chlorinated, brominated, but also non-halogenated derivatives. In addition to 22 known cylindrocyclophanes and carbamidocyclophanes, 27 putative congeners have been detected. Nine compounds, carbamidocyclophanes M-U, were isolated, and their structural elucidation by 1D and 2D NMR experiments in combination with HRMS and ECD analysis revealed that they are brominated analogues of chlorinated carbamidocyclophanes. Quantification of the carbamidocyclophanes showed that chloride is the preferably utilized halide, but incorporation is reduced in the presence of bromide. Evaluation of the antibacterial activity of 30 [7.7]paracyclophanes and related derivatives against selected pathogenic Gram-positive and Gram-negative bacteria exhibited remarkable effects especially against methicillin- and vancomycin-resistant staphylococci and Mycobacterium tuberculosis. For deeper insights into the mechanisms of biosynthesis, the carbamidocyclophane biosynthetic gene cluster in Nostoc sp. CAVN2 was studied. The gene putatively coding for the carbamoyltransferase has been identified. Based on bioinformatic analyses, a possible biosynthetic assembly is discussed.
dc.language.isoenen
dc.titleEffects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2.en
dc.typeArticleen
dc.contributor.departmentHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS),Saarland 9 University, 66123 Saarbrücken, Germany.en
dc.identifier.journalMarine drugsen
refterms.dateFOA2018-06-13T02:22:49Z
html.description.abstractIn this study, the influence of halide ions on [7.7]paracyclophane biosynthesis in the cyanobacterium Nostoc sp. CAVN2 was investigated. In contrast to KI and KF, supplementation of the culture medium with KCl or KBr resulted not only in an increase of growth but also in an up-regulation of carbamidocyclophane production. LC-MS analysis indicated the presence of chlorinated, brominated, but also non-halogenated derivatives. In addition to 22 known cylindrocyclophanes and carbamidocyclophanes, 27 putative congeners have been detected. Nine compounds, carbamidocyclophanes M-U, were isolated, and their structural elucidation by 1D and 2D NMR experiments in combination with HRMS and ECD analysis revealed that they are brominated analogues of chlorinated carbamidocyclophanes. Quantification of the carbamidocyclophanes showed that chloride is the preferably utilized halide, but incorporation is reduced in the presence of bromide. Evaluation of the antibacterial activity of 30 [7.7]paracyclophanes and related derivatives against selected pathogenic Gram-positive and Gram-negative bacteria exhibited remarkable effects especially against methicillin- and vancomycin-resistant staphylococci and Mycobacterium tuberculosis. For deeper insights into the mechanisms of biosynthesis, the carbamidocyclophane biosynthetic gene cluster in Nostoc sp. CAVN2 was studied. The gene putatively coding for the carbamoyltransferase has been identified. Based on bioinformatic analyses, a possible biosynthetic assembly is discussed.


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