Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners

Nicolas A. Frank
,
Márió Széles
,
Sergi H. Akone
,
Sari Rasheed
,
Stephan Hüttel
,
Simon Frewert
,
Mostafa M. Hamed
,
Jennifer Herrmann
ORCID logo ,
Soeren M. M. Schuler
,
Anna K. H. Hirsch
,
Rolf Müller
*
Version 1 : Received: 13 July 2021 / Approved: 14 July 2021 / Online: 14 July 2021 (10:03:32 CEST)

A peer-reviewed article of this Preprint also exists.

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. Molecules 2021, 26, 4929. 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. Molecules 2021, 26, 4929.

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.

Keywords

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

Subject

Chemistry and Materials Science, Analytical Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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