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Structure and Biosynthetic Assembly of Piscibactin, a Siderophore from Photobacterium damselae subsp. piscicida , Predicted from Genome Analysis
Author(s) -
Souto Alba,
Montaos Marcos A.,
Rivas Amable J.,
Balado Miguel,
Osorio Carlos R.,
Rodríguez Jaime,
Lemos Manuel L.,
Jiménez Carlos
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200818
Subject(s) - siderophore , biosynthesis , gene cluster , photobacterium , genome , microbiology and biotechnology , chemistry , gene , biology , biochemistry , computational biology , stereochemistry , genetics , bacteria , vibrio
From the cultures of Photobacterium damselae subsp. piscicida , the aetiological agent of fish pasteurellosis, a new siderophore named piscibactin ( 1 ), was isolated as its gallium and iron(III) complexes along with a possible intermediate of its biosynthesis, prepiscibactin ( 2 ). Analysis of the gene cluster involved in the siderophore biosynthesis allowed the partial prediction of the structures. Thus, an NRPS‐mediated mechanism similar to that for yersiniabactin was suggested by protein sequence comparisons. The final structures were solved by NMR and MS methods and by DFT molecular modeling. The results obtained in the structural and functional characterization of piscibactin enabled the proposal of a biosynthetic pathway.