Ruckerbactin Produced by YRB Is a Diastereomer of the Siderophore Trivanchrobactin Produced by DS40M4.

TitleRuckerbactin Produced by YRB Is a Diastereomer of the Siderophore Trivanchrobactin Produced by DS40M4.
Publication TypeJournal Article
Year of Publication2022
AuthorsThomsen E, Reitz ZL, Stow PR, Dulaney K, Butler A
JournalJ Nat Prod
Volume85
Issue1
Pagination264-269
Date Published2022 01 28
ISSN1520-6025
KeywordsCircular Dichroism, Peptides, Siderophores, Spectrum Analysis, Stereoisomerism, Vibrio, Yersinia ruckeri
Abstract

The Gram-negative bacterium is the causative agent for enteric red mouth disease in salmonids. The genome of YRB contains a biosynthetic gene cluster encoding the biosynthesis of catechol siderophores that are diastereomeric with the known vanchrobactin class of siderophores, (DHBArgSer). Ruckerbactin (), produced by YRB, was found to be the linear tris-l-serine ester composed of l-arginine and 2,3-dihydroxybenzoic acid, (DHBArgSer). The biscatechol, (DHBArgSer) (), and monocatechol, DHBArgSer (), compounds were also isolated and characterized. The macrolactone of ruckerbactin was not detected. The presence of Arg in ruckerbactin makes it the diastereomer of trivanchrobactin with Arg. The electronic circular dichroism spectra of Fe(III)-ruckerbactin and Fe(III)-trivanchrobactin reveal the opposite enantiomeric configurations at the Fe(III) sites. Fe(III)-ruckerbactin adopts the Δ configuration, and Fe(III)-trivanchrobactin adopts the Λ configuration. YRB was also found to produce the antimicrobial agent holomycin ().

DOI10.1021/acs.jnatprod.1c01047
Alternate JournalJ Nat Prod
PubMed ID34942075