Structure and biosynthesis of amychelin, an unusual mixed-ligand siderophore from Amycolatopsis sp. AA4. Author Mohammad Seyedsayamdost, Matthew Traxler, Shao-Liang Zheng, Roberto Kolter, Jon Clardy Publication Year 2011 Type Journal Article Abstract Actinobacteria generate a large number of structurally diverse small molecules with potential therapeutic value. Genomic analyses of this productive group of bacteria show that their genetic potential to manufacture small molecules exceeds their observed ability by roughly an order of magnitude, and this revelation has prompted a number of studies to identify members of the unknown majority. As a potential window into this cryptic secondary metabolome, pairwise assays for developmental interactions within a set of 20 sequenced actinomycetes were carried out. These assays revealed that Amycolatopsis sp. AA4, a so-called "rare" actinomycete, produces a novel siderophore, amychelin, which alters the developmental processes of several neighboring streptomycetes. Using this phenotype as an assay, we isolated amychelin and solved its structure by NMR and MS methods coupled with an X-ray crystallographic analysis of its Fe-complex. The iron binding affinity of amychelin was determined using EDTA competition assays, and a biosynthetic cluster was identified and annotated to provide a tentative biosynthetic scheme for amychelin. Keywords Molecular Structure, Models, Molecular, Ligands, Crystallography, X-Ray, Phenotype, Actinomycetales, Iron, Siderophores Journal J Am Chem Soc Volume 133 Issue 30 Pages 11434-7 Date Published 2011 Aug 03 ISSN Number 1520-5126 DOI 10.1021/ja203577e Alternate Journal J Am Chem Soc PMCID PMC3144690 PMID 21699219 PubMedPubMed CentralGoogle ScholarBibTeXEndNote X3 XML