Open AccessBacillibactins E and F from a Marine Sponge-Associated Bacillus sp.
Author(s) -
Qihao Wu,
Kurt Throckmorton,
Mitasree Maity,
Marc G. Chevrette,
D. C. Braun,
Scott R. Rajski,
Cameron R. Currie,
Michael G. Thomas
Publication year - 2020
Publication title -
journal of natural products
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.976
H-Index - 139
eISSN - 1520-6025
pISSN - 0163-3864
DOI - 10.1021/acs.jnatprod.0c01170
Subject(s) - sponge , moiety , stereochemistry , enterobactin , siderophore , benzoic acid , chemistry , bacillus subtilis , biology , biochemistry , bacteria , botany , genetics , gene
Chemical investigation of a marine sponge-associated Bacillus sp. led to the discovery of bacillibactins E and F ( 1 and 2 ). Despite containing the well-established cyclic triester core of iron-binding natural products such as enterobactin, bacillibactins E and F ( 1 and 2 ) are the first bacterial siderophores that contain nicotinic and benzoic acid moieties. The structures of the new compounds, including their absolute configurations, were determined by extensive spectroscopic analyses and Marfey's method. A plausible biosynthetic pathway to 1 and 2 is proposed; this route bears great similarity to other previously established bacillibactin-like pathways but appears to differentiate itself by a promiscuous DhbE, which likely installs the nicotinic moiety of 1 and the benzoic acid group of 2 .