Pseudomonas siderophores: A mild and selective halogenation procedure of the chromophoric moiety of pyoverdins

In the course of the purification procedure of pyoverdins produced by Pseudomonas aeruginosa ATCC 15692 in large batch cultures, a minor peptidic chlorinated siderophore was isolated. This compound possesses the same peptidic moiety as the three major pyoverdins isolated from this strain, but it is...

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Bibliographic Details
Published in:Tetrahedron letters 1997-01, Vol.38 (1), p.97-100
Main Authors: Hennard, Christophe, Machi, Bachir, Kyslík, Pavel, Abdallah, Mohamed A.
Format: Article
Language:English
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Summary:In the course of the purification procedure of pyoverdins produced by Pseudomonas aeruginosa ATCC 15692 in large batch cultures, a minor peptidic chlorinated siderophore was isolated. This compound possesses the same peptidic moiety as the three major pyoverdins isolated from this strain, but it is bound to a chlorinated chromophore derived from 5-chloro-2,3-diamino-6,7-dihydroxyquinoline. A mechanism for the formation of these compounds is suggested and a procedure for the preparation of halopyoverdins is described. A mild and selective halogenation procedure of pyoverdins at position C-5 of their chromophoric moiety is described and a two step electron transfer mechanism for the formation of these 5-halopyoverdins is suggested.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(96)02224-1