Effects of halide ions on the carbamidocyclophane biosynthesis in nostoc sp. CAVN2

M. Preisitsch, S.E. Heiden, M. Beerbaum, T.H.J. Niedermeyer, M. Schneefeld, J. Herrmann, J. Kumpfmüller, A. Thürmer, I. Neidhardt, C. Wiesner, R. Daniel, R. Müller, F.-C. Bange, P. Schmieder, T. Schweder, S. Mundt

Publikation: Beitrag in FachzeitschriftArtikelBegutachtung

Abstract

In 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 MU, were isolated, and their structural elucidation by 1D and 2DNMRexperiments 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.
OriginalspracheEnglisch
Aufsatznummer21
Seiten (von - bis)21
FachzeitschriftMarine Drugs
Jahrgang14
Ausgabenummer1
DOIs
PublikationsstatusVeröffentlicht - 20 Jän. 2016
Extern publiziertJa

IMC Forschungsschwerpunkte

  • Medical biotechnology

ÖFOS 2012 - Österreichischen Systematik der Wissenschaftszweige

  • 304005 Medizinische Biotechnologie

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