Synthesis and structural modeling of the amphiphilic siderophore rhizobactin-1021 and its analogs.
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.
Fadeev
Evgeny A
EA
Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.
Luo
Minkui
M
Groves
John T
JT
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D002951:Citrates / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D017262:Siderophores / Q000737:chemistry*; D016962:Sinorhizobium meliloti / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry*
D000475:Alkenes; D002951:Citrates; D017262:Siderophores; D013501:Surface-Active Agents; C505710:rhizobactin-1021