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Rhodotorulic acid

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Rhodotorulic acid
Names
IUPAC name N-propyl]-3,6-dioxopiperazin-2-yl]propyl]-N-hydroxyacetamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ECHA InfoCard 100.038.786 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • CC(=O)N(CCCC1C(=O)NC(C(=O)N1)CCCN(C(=O)C)O)O
Properties
Chemical formula C14H24N4O6
Molar mass 344.368 g·mol
Density 1.277 g/cm
Solubility in water 0.96 g/cm (25 °C) @ pH 7 (water)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Rhodotorulic acid is the smallest of the 2,5-diketopiperazine family of hydroxamate siderophores which are high-affinity chelating agents for ferric iron, produced by bacterial and fungal phytopathogens for scavenging iron from the environment. It is a tetradentate ligand, meaning it binds one iron atom in four locations (two hydroxamate and two lactam moieties), and forms Fe2(siderophore)3 complexes to fulfill an octahedral coordination for iron.

Rhodotorulic acid occurs in basidiomycetous yeasts and was found to retard the spore germination of the fungus Botrytis cinerea. In combination with yeast Rhodotorula glutinis it was found to be effective in the biocontrol of iprodione-resistant B. cinerea of apple wounds caused by the disease.

References

  1. Borthwick AD, Da Costa NC (2017). "2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity". Critical Reviews in Food Science and Nutrition. 57 (4): 718–742. doi:10.1080/10408398.2014.911142. PMID 25629623. S2CID 1334464.
  2. Hider RC, Kong X (May 2010). "Chemistry and biology of siderophores". Natural Product Reports. 27 (5): 637–657. doi:10.1039/B906679A. PMID 20376388.
  3. Butler, Alison (2007). Biological Inorganic Chemistry: Structure & Reactivity. pp. 151–156. ISBN 978-1891389436.
  4. Van der Helm D, Winkelmann G (February 1994). "Hydroxamates and Polycarboxylates as Ion Transport Agents (Siderophores)". In Winkelmann, G., Winge, D. (eds.). Metal ions in fungi. Vol. 11. New York: Marcel Dekker Inc. pp. 39–98. ISBN 0-8247-9172-X.
  5. Sansone G, Rezza I, Calvente V, Benuzzi D, de Tosetti MI (March 2005). "Control of Botrytis cinerea strains resistant to iprodione in apple with rhodotorulic acid and yeasts". Postharvest Biology and Technology. 35 (3): 245–251. doi:10.1016/j.postharvbio.2004.09.005.
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