Structure and Biosynthesis of Crocagins

Polycyclic Posttranslationally Modified Ribosomal Peptides from Chondromyces crocatus

Konrad Viehrig, Frank Surup, Carsten Volz, Jennifer Herrmann, Antoine Abou Fayad, Sebastian Adam, Jesko Köhnke, Dirk Trauner, Rolf Müller

Research output: Contribution to journalArticle

Abstract

Secondary metabolome mining efforts in the myxobacterial multiproducer of natural products, Chondromyces crocatus Cm c5, resulted in the isolation and structure elucidation of crocagins, which are novel polycyclic peptides containing a tetrahydropyrrolo[2,3-b]indole core. The gene cluster was identified through an approach combining genome analysis, targeted gene inactivation in the producer, and in vitro experiments. Based on our findings, we developed a biosynthetic scheme for crocagin biosynthesis. These natural products are formed from the three C-terminal amino acids of a precursor peptide and thus belong to a novel class of ribosomally synthesized and post-translationally modified peptides (RiPPs). We demonstrate that crocagin A binds to the carbon storage regulator protein CsrA, thereby inhibiting the ability of CsrA to bind to its cognate RNA target.

Original languageEnglish (US)
Pages (from-to)7407-7410
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number26
DOIs
StatePublished - 2017

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Biosynthesis
Peptides
Genes
Biological Products
RNA
Amino acids
Carbon
Proteins
Amino Acids
Experiments

Keywords

  • biosynthesis
  • inhibitors
  • myxobacteria
  • natural products
  • RiPPs

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Structure and Biosynthesis of Crocagins : Polycyclic Posttranslationally Modified Ribosomal Peptides from Chondromyces crocatus. / Viehrig, Konrad; Surup, Frank; Volz, Carsten; Herrmann, Jennifer; Abou Fayad, Antoine; Adam, Sebastian; Köhnke, Jesko; Trauner, Dirk; Müller, Rolf.

In: Angewandte Chemie - International Edition, Vol. 56, No. 26, 2017, p. 7407-7410.

Research output: Contribution to journalArticle

Viehrig, K, Surup, F, Volz, C, Herrmann, J, Abou Fayad, A, Adam, S, Köhnke, J, Trauner, D & Müller, R 2017, 'Structure and Biosynthesis of Crocagins: Polycyclic Posttranslationally Modified Ribosomal Peptides from Chondromyces crocatus', Angewandte Chemie - International Edition, vol. 56, no. 26, pp. 7407-7410. https://doi.org/10.1002/anie.201612640
Viehrig, Konrad ; Surup, Frank ; Volz, Carsten ; Herrmann, Jennifer ; Abou Fayad, Antoine ; Adam, Sebastian ; Köhnke, Jesko ; Trauner, Dirk ; Müller, Rolf. / Structure and Biosynthesis of Crocagins : Polycyclic Posttranslationally Modified Ribosomal Peptides from Chondromyces crocatus. In: Angewandte Chemie - International Edition. 2017 ; Vol. 56, No. 26. pp. 7407-7410.
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