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Angew Chem Int Ed Engl. 2017 Jun 19;56(26):7407-7410. doi: 10.1002/anie.201612640. Epub 2017 May 23.

Structure and Biosynthesis of Crocagins: Polycyclic Posttranslationally Modified Ribosomal Peptides from Chondromyces crocatus.

Author information

1
Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Center for Infection Research and Pharmaceutical Biotechnology, Saarland University, Campus, Building E8.1, 66123, Saarbrücken, Germany.
2
Helmholtz Center for Infection Research (HZI), Department Microbial Drugs, Inhoffenstraße 7, 38124, Braunschweig, Germany.
3
German Centre for Infection Research (DZIF), Partner Site Hannover-Braunschweig, Germany.
4
Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377, Munich, Germany.

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.

KEYWORDS:

RiPPs; biosynthesis; inhibitors; myxobacteria; natural products

PMID:
28544148
DOI:
10.1002/anie.201612640

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