@article{111, author = {O. Baars and X. Zhang and M.I. Gibson and A.T. Stone and F.M.M. Morel and M.R. Seyedsayamdost}, title = {Crochelins: Siderophores with an Unprecedented Iron-Chelating Moiety from the Nitrogen-Fixing Bacterium Azotobacter chroococcum}, abstract = {Microbes use siderophores to access essential iron resources in the environment. Over 500 siderophores are known, but they utilize a small set of common moieties to bind iron. Azotobacter chroococcum expresses iron-rich nitrogenases, with which it reduces N2. Though an important agricultural inoculant, the structures of its iron-binding molecules remain unknown. Here, the {\textquotedblleft}chelome{\textquotedblright} of A. chroococcum is examined using small molecule discovery and bioinformatics. The bacterium produces vibrioferrin and amphibactins as well as a novel family of siderophores, the crochelins. Detailed characterization shows that the most abundant member, crochelin A, binds iron in a hexadentate fashion using a new iron-chelating γ-amino acid. Insights into the biosynthesis of crochelins and the mechanism by which iron may be removed upon import of the holo-siderophore are presented. This work expands the repertoire of iron-chelating moieties in microbial siderophores. {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim}, year = {2018}, journal = {Angewandte Chemie - International Edition}, volume = {57}, number = {2}, pages = {536-541}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85042085445\&doi=10.1002\%2fanie.201709720\&partnerID=40\&md5=f1fb723554e7fb807d8e622fd12b2265}, doi = {10.1002/anie.201709720}, }