Structure and biosynthesis of amychelin, an unusual mixed-ligand siderophore from amycolatopsis sp. AA4

Mohammad R. Seyedsayamdost, Matthew F. Traxler, Shao Liang Zheng, Roberto Kolter, Jon Clardy

Research output: Contribution to journalArticle

53 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)11434-11437
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number30
DOIs
StatePublished - Aug 3 2011

Fingerprint

Siderophores
Actinobacteria
Biosynthesis
Assays
Ligands
Metabolome
Edetic Acid
Molecules
Ethylenediaminetetraacetic acid
Iron
X-Rays
Bacteria
Phenotype
Nuclear magnetic resonance
X rays
Therapeutics

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry

Cite this

Seyedsayamdost, Mohammad R. ; Traxler, Matthew F. ; Zheng, Shao Liang ; Kolter, Roberto ; Clardy, Jon. / Structure and biosynthesis of amychelin, an unusual mixed-ligand siderophore from amycolatopsis sp. AA4. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 30. pp. 11434-11437.
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Structure and biosynthesis of amychelin, an unusual mixed-ligand siderophore from amycolatopsis sp. AA4. / Seyedsayamdost, Mohammad R.; Traxler, Matthew F.; Zheng, Shao Liang; Kolter, Roberto; Clardy, Jon.

In: Journal of the American Chemical Society, Vol. 133, No. 30, 03.08.2011, p. 11434-11437.

Research output: Contribution to journalArticle

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