Rhodotorulic acid

Rhodotorulic acid
Names
	IUPAC name N-[3-[5-[3-[Acetyl(hydroxy)amino]propyl]-3,6-dioxopiperazin-2-yl]propyl]-N-hydroxyacetamide
Identifiers
CAS Number	18928-00-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:84731 ;
ECHA InfoCard	100.038.786
PubChem CID	29337;
UNII	61F3VBQ4G5 ;
	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−1
Density	1.277 g/cm3
Solubility in water	0.96 g/cm3 (25 °C) @ pH 7 (water)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Rhodotorulic acid is the smallest of the 2,5-diketopiperazine family[1] of hydroxamate siderophores which are high-affinity chelating agents for ferric iron, produced by bacterial and fungal phytopathogens for scavenging iron from the environment.[2] It is a tetradentate ligand, meaning it binds one iron atom in four locations (two hydroxamate and two ketone moieties), and forms Fe₂(siderophore)₃ complexes to fulfill an octahedral coordination for iron.[3]

Rhodotorulic acid occurs in basidiomycetous yeasts [4] and was found to retard the spore germination of the fungus Botrytis cinerea. In combination with yeast R. glutinis it was found to be effective in the biocontrol [5] of iprodione-resistant B. cinerea of apple wounds caused by the disease.

References

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.
Hider RC, Kong X (May 2010). "Chemistry and biology of siderophores". Natural Product Reports. 27 (5): 637–657. doi:10.1039/B906679A. PMID 20376388.
Butler, Alison (2007). Biological Inorganic Chemistry: Structure & Reactivity. pp. 151–156. ISBN 978-1891389436.
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. 11. New York: Marcel Dekker Inc. pp. 39–98. ISBN 0-8247-9172-X.
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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[pmid25629623-1] 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.

[pmid20376388-2] 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. 11. New York: Marcel Dekker Inc. pp. 39–98. ISBN 0-8247-9172-X.

[doi10.1016/j.postharvbio.2004.09.005-5] 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.