Amavadin
Chemical compound
From Wikipedia, the free encyclopedia
Amavadin is a vanadium-containing coordination complex that occurs naturally. It is found found in three species of poisonous Amanita mushrooms: A. muscaria, A. regalis, and A. velatipes.[1]
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| IUPAC name
bis[N-[(1S)-1-(carboxy-κO)ethyl]-N-(hydroxy-κO)-L-alaninato(2-)-.κN,κO]-vanadium | |
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| Properties | |
| [V{NO[CH(CH3)CO2]2}2]2− | |
| Molar mass | 398.94 g/mol |
| Appearance | Light blue in solution |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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History and structure
The ligand found in amavadin was first synthesized in 1954.[2] Amavadin was first isolated and identified in 1972 by Kneifel and Bayer.[3] In 1993, it was discovered by X-ray crystallography that amavadin is not a vanadyl ion complex. Instead, it is an octacoordinated vanadium(IV) complex. This vanadium center is bonded to two tetradentate ligands derived from N-hydroxyimino-2,2'-dipropionic acid, H3(HIDPA), ligands.[4] The ligands coordinate through the nitrogen and the three oxygen centers.
The anionic complex is blue. It is an eight-coordinate vanadium complex.[1] A Ca2+ cation is often used to crystallize amavadin to obtain a good quality X-ray diffraction.[1] Oxidized amavadin can be isolated as its PPh4+ salt. The oxidized form contains vanadium(V), which has been studied by NMR spectroscopy.[5]
Amavadin contains vanadium(IV). Initially, amavadin was thought to have a vanadyl, VO2+, center.[6]
Amavadin is a C2-symmetric anion with a 3− charge. The twofold axis bisects the vanadium atom perpendicular to the two NO ligands. The anion features five chiral centers, one at vanadium and the four carbon atoms having S stereochemistry.[1] There are two possible diastereomers for the ligands, (S,S)-(S,S)-Δ and (S,S)-(S,S)-Λ.
Preparation
Biological function
The biological function of amavadin is unknown. It has been speculated that it uses H2O2 and acts as a peroxidase to aid the regeneration of damaged tissues.[5] Amavadin may serve as a toxin for protection of the mushroom.[7]
