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Nitro versus Hydroxamate in Siderophores of Pathogenic Bacteria: Effect of Missing Hydroxylamine Protection in Malleobactin Biosynthesis
Author(s) -
Franke Jakob,
Ishida Keishi,
IshidaIto Mie,
Hertweck Christian
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201303196
Subject(s) - hydroxylamine , siderophore , nitro , virulence , bacteria , microbiology and biotechnology , chemistry , biology , gene , biochemistry , genetics , organic chemistry , alkyl
The elusive structure of malleobactin, a virulence factor of pathogens belonging to the Burkholderia mallei family, was finally unveiled by genetic and chemical analyses. The novel nitro‐substituted siderophore is derived from an unusual, unprotected hydroxylamine, which undergoes spontaneous oxidation, as shown by in vitro assays and detection of analogues featuring hydroxylamino, nitroso, and azoxide groups.