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http://hdl.handle.net/2183/39553 Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+ Complex
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De la Fuente, Carmen
Segade Parrado, Yuri
Valderrama Pereira, Andrea Katherine
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de la Fuente, M. C.; Segade, Y.; Valderrama, K.; Rodríguez, J.; Jiménez, C. Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+ Complex. Org. Lett. 2021, 23 (2), 340–345. https://doi.org/10.1021/acs.orglett.0c03850.
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Abstract
[Abstract] 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 β-hydroxy-2,4-disubstituted thiazoline moiety and the convenient protecting groups was a key step in this synthesis.
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Author accepted manuscript