Advertisement

Bioinorganic and bio-organic studies of rhizobactin, a structurally novel siderophore related to the opines

  • M. J. Smith
Part of the Beltsville Symposia in Agricultural Research book series (BSAR, volume 14)

Abstract

The recent structure elucidation of rhizobactin, N 2-[2-[D-(l-carboxyethyl)-amino]ethyl]-N 6-L-(3-carboxy-3-)hydroxy-l-oxopropyl)-L-lysine, from Rhizobium meliloti DM4 disclosed a third chemical class of microbial siderophores (Gr. sidero = iron; phore = bearer; Smith et al., 1985); the ethylenediamine ligand also was unprecedented in a natural product. Yet determination of the absolute configuration and proof of the entire structure awaited total synthesis. This has been accomplished (Smith, 1989) and substantiates the conclusion that the siderophore is related in structure and activity to other N 2-substituted amino acids termed opines (Smith and Neilands, 1984a, b). As iminocarboxylic acids, opines, rhizobactin and phytosiderophores possess substantially reduced selectivities for iron(III). Such compounds could enhance the bioavailability of additional essential metal ions in the rhizosphere.

Key words

opine NMR Rhizobium siderophore 

References

  1. Emery T 1971 Biochem. 10, 1483–1488.CrossRefGoogle Scholar
  2. Demarco A et al. 1978 Biopolymers 17, 617–636 and 637–650.CrossRefGoogle Scholar
  3. Garbett K et al. 1971 J. Chem. Soc. (A) 3433–3436.Google Scholar
  4. Lippard S J et al. 1967 Inorg. Chem. 6, 1825–1831.CrossRefGoogle Scholar
  5. Smith M J 1989 Tetrahedron Lett. 30, 313–316.CrossRefGoogle Scholar
  6. Smith M J et al. 1985 J. Am. Chem. Soc. 107, 1739–1743.CrossRefGoogle Scholar
  7. Smith M J and Neilands J B 1984a J. Plant Nutri. 7, 449–458.CrossRefGoogle Scholar
  8. Smith M J and Neilands J B 1984b In Molecular Strategies for Crop Protection, Vol. 48. Eds. C J Arntzen and C Ryan. Alan R. Liss, Inc. New York, pp 157–168.Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 1991

Authors and Affiliations

  • M. J. Smith
    • 1
  1. 1.Department of ChemistryColumbia UniversityNew YorkUSA

Personalised recommendations