Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+ Complex

The siderophore piscibactin is a key virulence factor involved in the iron uptake of pathogenic bacteria Photobacterium damselae subsp. piscicida and Vibrio anguillarum, responsible for the fish diseases photobacterioisis (pasteurellosis) and vibriosis, respectively. A convergent total synthesis of its Ga3+ complex using L-/D-cysteine as chiral agents and Meldrum's acid is described. A Staudinger reduction/Aza-Wittig process in the synthesis of the acid-sensitive beta-hydroxy-2,4-disubstituted thiazoline moiety and the convenient protecting groups was a key step in this synthesis.

Automated summary

The siderophore piscibactin is a key virulence factor involved in iron uptake by pathogenic bacteria causing fish diseases. A convergent total synthesis of its Ga3+ complex was described using L-/D-cysteine as chiral agents and Meldrum's acid. A Staudinger reduction/Aza-Wittig process was a key step in the synthesis of the acid-sensitive beta-hydroxy-2,4-disubstituted thiazoline moiety.