Chemistry:Rhodotorulic acid
| |
| Names | |
|---|---|
| IUPAC name
N-[3-[5-[3-[Acetyl(hydroxy)amino]propyl]-3,6-dioxopiperazin-2-yl]propyl]-N-hydroxyacetamide
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
PubChem CID
|
|
| UNII | |
| |
| Properties | |
| C14H24N4O6 | |
| Molar mass | 344.368 g·mol−1 |
| Density | 1.277 g/cm3 |
| 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). | |
 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 lactam 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 Rhodotorula glutinis it was found to be effective in the biocontrol[5] of iprodione-resistant B. cinerea of apple wounds caused by the disease.
References
- ↑ "2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity". Critical Reviews in Food Science and Nutrition 57 (4): 718–742. 2017. doi:10.1080/10408398.2014.911142. PMID 25629623.
- ↑ "Chemistry and biology of siderophores". Natural Product Reports 27 (5): 637–657. May 2010. doi:10.1039/B906679A. PMID 20376388.
- ↑ Butler, Alison (2007). Biological Inorganic Chemistry: Structure & Reactivity. pp. 151–156. ISBN 978-1891389436.
- ↑ Winkelmann, G., ed (February 1994). "Hydroxamates and Polycarboxylates as Ion Transport Agents (Siderophores)". Metal ions in fungi. 11. New York: Marcel Dekker Inc. pp. 39–98. ISBN 0-8247-9172-X.
- ↑ "Control of Botrytis cinerea strains resistant to iprodione in apple with rhodotorulic acid and yeasts". Postharvest Biology and Technology 35 (3): 245–251. March 2005. doi:10.1016/j.postharvbio.2004.09.005.
 |  |
