Beilstein J. Org. Chem.2023,19, 909–917, doi:10.3762/bjoc.19.69
metabolites that were recovered in this study share a phenolic moiety with a thiazole or thiazoline substituent. This motif is present in many siderophores, e.g., in pyochelin [26], yersiniabactin [28], agrochelin [29], micacocidin [30], the Massilia-derived massiliachelin [18], as well as in piscibactin [31
PDF
Graphical Abstract
Figure 1:
Selected siderophores from β-proteobacteria.
Beilstein J. Org. Chem.2019,15, 1298–1303, doi:10.3762/bjoc.15.128
. A compound which was found to be predominantly produced under iron deficiency was subsequently isolated. Its structural characterization by spectroscopic and bioinformatic analyses revealed a previously not known diastereomer of the cytotoxic alkaloid agrochelin. The structure of this natural
product, which was named massiliachelin, corresponds to the assembly line encoded by the identified siderophore locus.
Keywords: agrochelin; genome mining; Massilia; massiliachelin; siderophore; stereochemistry; Introduction
In recent years, chemical investigations as well as genomics led to the
production and complexing properties [15]. Therefore, we decided to initially focus our genome mining efforts on the micacocidin-type cluster in Massilia sp. NR 4-1. Here, we report the outcome of this study, which led to the identification of a previously unrecognized agrochelin epimer and, furthermore
PDF
Graphical Abstract
Figure 1:
A) Organization of the micacocidin-type gene cluster from Massilia sp. NR 4-1 (top) and of the mic ...