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

Evgeny A. Fadeev, Minkui Luo, John Taylor Groves

Research output: Contribution to journalArticle

4 Scopus citations

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 languageEnglish (US)
Pages (from-to)3771-3774
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume15
Issue number16
DOIs
StatePublished - Aug 15 2005

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Keywords

  • Acinetoferrin
  • Amphiphile
  • Iron
  • Mycobactin
  • Structure

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