Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners

Version 1 : Received: 13 July 2021 / Approved: 14 July 2021 / Online: 14 July 2021 (10:03:32 CEST)

How to cite: Frank, N.A.; Széles, M.; Akone, S.H.; Rasheed, S.; Hüttel, S.; Frewert, S.; Hamed, M.M.; Herrmann, J.; Schuler, S.M.M.; Hirsch, A.K.H.; Müller, R. Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners. Preprints 2021, 2021070315 (doi: 10.20944/preprints202107.0315.v1). Frank, N.A.; Széles, M.; Akone, S.H.; Rasheed, S.; Hüttel, S.; Frewert, S.; Hamed, M.M.; Herrmann, J.; Schuler, S.M.M.; Hirsch, A.K.H.; Müller, R. Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners. Preprints 2021, 2021070315 (doi: 10.20944/preprints202107.0315.v1).

Abstract

Myxobacteria represent a viable source of chemically diverse and biologically active secondary metabolites. The myxochelins are a well-studied family of catecholate-type siderophores produced by various myxobacterial strains. Here, we report the discovery, isolation and structure elucidation of three new myxochelins N1–N3 from the terrestrial myxobacterium Corallococcus sp. MCy9049, featuring an unusual nicotinic acid moiety. Precursor-directed biosynthesis (PDB) experiments and total synthesis were performed in order to confirm structures, improve access to pure compounds for bioactivity testing and to devise a biosynthesis proposal. The combined evaluation of metabolome and genome data covering myxobacteria supports the notion that the new myxochelin congeners reported here are in fact frequent side products of the known myxochelin A biosynthetic pathway in myxobacteria.

Subject Areas

Myxobacteria; myxochelin; nicotinic acid; secondary metabolites; natural product discovery; precursor-directed biosynthesis; total synthesis

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