Synthesis and structural modeling of the amphiphilic siderophore rhizobactin-1021 and its analogs

[Display omitted] We describe two convenient syntheses of rhizobactin-1021 ( Rz), a citrate-based siderophore amphiphile produced by the nitrogen-fixing root symbiont Rhizobium meliloti- 1021, and several analogs. Our approach features a singly amidated, tert-butyl-protected citrate intermediate tha...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2005-08, Vol.15 (16), p.3771-3774
Main Authors: Fadeev, Evgeny A., Luo, Minkui, Groves, John T.
Format: Article
Language:English
Subjects:
Acinetoferrin
Alkenes - chemical synthesis
Alkenes - chemistry
Amphiphile
Citrates - chemical synthesis
Citrates - chemistry
Crystallography, X-Ray
Iron
Models, Molecular
Molecular Conformation
Mycobactin
Siderophores - chemistry
Sinorhizobium meliloti - chemistry
Structure
Surface-Active Agents - chemistry
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Description
Summary:[Display omitted] We describe two convenient syntheses of rhizobactin-1021 ( Rz), a citrate-based siderophore amphiphile produced by the nitrogen-fixing root symbiont Rhizobium meliloti- 1021, and several analogs. Our approach features a singly amidated, tert-butyl-protected citrate intermediate that easily affords a variety of Rz analogs in the late stages of the synthesis. Structural modeling and the monolayer behavior of Rz and its metal complexes are consistent with a structural reorganization upon Rz-mediated iron chelation.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2005.05.114