Rhodotorulic acid
 | |
| Names | |
|---|---|
| IUPAC name
N-[3-[5-[3-[acetyl(hydroxy)amino]propyl]-3,
6-dioxopiperazin-2-yl]propyl]-N-hydroxyacetamide | |
| Identifiers | |
18928-00-2  | |
| ChEBI | CHEBI:84731  |
| Jmol 3D model | Interactive image |
| PubChem | 29337 |
| |
| Properties | |
| C14H24N4O6 | |
| Molar mass | 344.36 g/mol |
| Density | 1.277 g·cm−3 |
| 0,96 g·cm−3 (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). | |
| verify (what is ?) | |
| 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 (January 2015). "2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity". Critical reviews in food science and nutrition. doi:10.1080/10408398.2014.911142. PMID 18412344.
- ↑ 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, Biological Inorganic Chemistry: Structure & Reactivity, 2007, pp.151-156.
- ↑ Van der Helm D, Winkelmann G (February 1994). "Hydroxamates and Polycarboxylates as Ion Transport Agents (Siderophores)". In Winkelmann, G., Winge, D. 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.
External links
- Amazon.com - Biological Inorganic Chemistry on Amazon.com