Abstract
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.
Original language | English (US) |
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Pages (from-to) | 3771-3774 |
Number of pages | 4 |
Journal | Bioorganic and Medicinal Chemistry Letters |
Volume | 15 |
Issue number | 16 |
DOIs | |
State | Published - Aug 15 2005 |
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Molecular Medicine
- Molecular Biology
- Biochemistry
- Clinical Biochemistry
- Pharmaceutical Science
- Organic Chemistry
Keywords
- Acinetoferrin
- Amphiphile
- Iron
- Mycobactin
- Structure