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{{orphan|date=April 2010}} |
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{{chembox |
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| verifiedrevid = 409856282 |
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| ImageFile = Rhodotorulic acid.svg |
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| ImageFile = Rhodotorulic acid.svg |
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| ImageSize = 350px |
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| ImageSize = 200px |
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| IUPACName = N-propyl]-3, |
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| IUPACName = ''N''-propyl]-3,6-dioxopiperazin-2-yl]propyl]-''N''-hydroxyacetamide |
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6-dioxopiperazin-2-yl]propyl]-N-hydroxyacetamide |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| EINECS = |
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| EINECS = |
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| PubChem = 29337 |
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| PubChem = 29337 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 84731 |
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| SMILES = CC(=O)N(CCCC1C(=O)NC(C(=O)N1)CCCN(C(=O)C)O)O |
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| SMILES = CC(=O)N(CCCC1C(=O)NC(C(=O)N1)CCCN(C(=O)C)O)O |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 18928-00-2 |
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| CASNo = 18928-00-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 61F3VBQ4G5 |
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| InChI = |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>14</sub>H<sub>24</sub>N<sub>4</sub>O<sub>6</sub> |
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| C=14 | H=24 | N=4 | O=6 |
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| MolarMass = 344.36 g/mol |
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| Density = 1.277 g/cm<sup>3</sup> |
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| Density = 1.277 g·cm<sup>-3</sup> |
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| Solubility = 0.96 g/cm<sup>3</sup> (25 °C) @ pH 7 (water) |
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| Solubility = 0,96 g·cm<sup>-3</sup> (25 °C) @ pH 7 (water) |
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'''Rhodotorulic acid''' is a dihydroxamate-containing ] which is expressed by some ] for the purposes of sequestering insoluble ] iron(III) for organism growth. It has been implicated as a chiral recognition factor in the transport of iron(III). It is a tetradentate ligand, meaning it binds one iron atom in four locations (two ] and two ] moieties), and forms Fe<sub>2</sub>(siderophore)<sub>3</sub> complexes to fulfill an octahedral coordination for iron. It possesses a 2-fold symmetry axis passing through the heteroring.<ref>Butler, Alison, ''Biological Inorganic Chemistry: Structure & Reactivity'', 2007, pp.151-156.</ref> |
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'''Rhodotorulic acid''' is the smallest of the ] family<ref name="pmid25629623">{{cite journal |vauthors=Borthwick AD, Da Costa NC | title = 2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity | journal = Critical Reviews in Food Science and Nutrition | volume = 57 | issue = 4 | pages = 718–742 | date= 2017 | pmid = 25629623 | doi = 10.1080/10408398.2014.911142| s2cid = 1334464 }}</ref> of hydroxamate ] which are high-affinity chelating agents for ] iron, produced by ]l and fungal phytopathogens for scavenging iron from the environment.<ref name="pmid20376388">{{cite journal |vauthors=Hider RC, Kong X | title = Chemistry and biology of siderophores | journal = Natural Product Reports | volume = 27 | issue = 5 | pages = 637–657 | date= May 2010 | pmid = 20376388 | doi = 10.1039/B906679A }}</ref> It is a tetradentate ligand, meaning it binds one iron atom in four locations (two ] and two ] moieties), and forms Fe<sub>2</sub>(siderophore)<sub>3</sub> complexes to fulfill an octahedral coordination for iron.<ref>{{cite book | author = Butler, Alison | title = Biological Inorganic Chemistry: Structure & Reactivity | date = 2007 | pages = 151–156 | isbn = 978-1891389436}}</ref> |
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Rhodotorulic acid occurs in basidiomycetous ]<ref>{{cite book|title= Metal ions in fungi |date = February 1994 |publisher= Marcel Dekker Inc |location= New York | isbn= 0-8247-9172-X | volume = 11 | pages=39–98 |vauthors=Van der Helm D, Winkelmann G | editor= Winkelmann, G. |editor2=Winge, D. |chapter= Hydroxamates and Polycarboxylates as Ion Transport Agents (Siderophores) }}</ref> and was found to retard the spore germination of the fungus '']''. In combination with yeast ''Rhodotorula glutinis'' it was found to be effective in the ]<ref name="doi10.1016/j.postharvbio.2004.09.005">{{cite journal |vauthors=Sansone G, Rezza I, Calvente V, Benuzzi D, de Tosetti MI | title = Control of Botrytis cinerea strains resistant to iprodione in apple with rhodotorulic acid and yeasts | journal = Postharvest Biology and Technology | volume = 35 | issue = 3 | pages = 245–251| date= March 2005 | doi = 10.1016/j.postharvbio.2004.09.005 }}</ref> of ]-resistant ''B. cinerea'' of apple wounds caused by the disease. |
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== References == |
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== References == |
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<!--- See http://en.wikipedia.org/Wikipedia:Footnotes on how to create references using <ref></ref> tags which will then appear here automatically --> |
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{{Reflist}} |
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{{Reflist}} |
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== External links == |
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* - ''Biological Inorganic Chemistry'' on Amazon.com |
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{{DEFAULTSORT:Rhodotorulic Acid}} |
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{{DEFAULTSORT:Rhodotorulic Acid}} |
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