Amavadin: Difference between revisions
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The ligand found in amavadin was first synthesized in 1954.<ref>{{cite journal | author = Fu, S-C.J.; Birnbaum, S.M.; Greenstein, J.P. | title = Influence of Optically Active Acyl Groups on the Enzymatic Hydrolysis of N-Acylated-L-amino Acids | journal = J. Am. Chem. Soc. | year = 1954 | volume = 76 | issue = 23 | pages = 6054–6058 | doi = 10.1021/ja01652a057}}</ref> Amavadin contains vanadium(IV). Initially, amavadin was thought to have a vanadyl, VO<sup>2+</sup>, center. In 1993, it was discovered by crystallographic characterization that amavadin is not a [[vanadyl ion]] compound. Instead, it is an octacoordinated vanadium(IV) complex. This complex is bonded to two tetradentate ligands derived from N-hydroxyimino-2,2'-dipropionic acid, H<sub>3</sub>(HIDPA), ligands.<ref>{{cite journal | author = Armstrong, E.M.; Beddoes, R.L.; Calviou, L.J.; Charnock, J.M.; Collison, D.; Ertok, N.; Naismith, J.H.; Garner, C.D. | title = The Chemical Nature of Amavadin | journal = J. Am. Chem. Soc. | year = 1993 | volume = 115 | issue = 2 | pages = 807–808 | doi = 10.1021/ja00055a073}}</ref> The ligands coordinate through the nitrogen and the three oxygen centers. |
The ligand found in amavadin was first synthesized in 1954.<ref>{{cite journal | author = Fu, S-C.J.; Birnbaum, S.M.; Greenstein, J.P. | title = Influence of Optically Active Acyl Groups on the Enzymatic Hydrolysis of N-Acylated-L-amino Acids | journal = J. Am. Chem. Soc. | year = 1954 | volume = 76 | issue = 23 | pages = 6054–6058 | doi = 10.1021/ja01652a057}}</ref> Amavadin contains vanadium(IV). Initially, amavadin was thought to have a vanadyl, VO<sup>2+</sup>, center. In 1993, it was discovered by crystallographic characterization that amavadin is not a [[vanadyl ion]] compound. Instead, it is an octacoordinated vanadium(IV) complex. This complex is bonded to two tetradentate ligands derived from N-hydroxyimino-2,2'-dipropionic acid, H<sub>3</sub>(HIDPA), ligands.<ref>{{cite journal | author = Armstrong, E.M.; Beddoes, R.L.; Calviou, L.J.; Charnock, J.M.; Collison, D.; Ertok, N.; Naismith, J.H.; Garner, C.D. | title = The Chemical Nature of Amavadin | journal = J. Am. Chem. Soc. | year = 1993 | volume = 115 | issue = 2 | pages = 807–808 | doi = 10.1021/ja00055a073}}</ref> The ligands coordinate through the nitrogen and the three oxygen centers. |
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Amavadin is a C<sub>2</sub>-symmetric anion with a 2− charge. The |
Amavadin is a C<sub>2</sub>-symmetric anion with a 2− 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.<ref name="Berry" /> There are two possible diastereomers for the ligands, (''S'',''S'')-(''S'',''S'')-Δ and (''S'',''S'')-(''S'',''S'')-Λ. |
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[[Image:AmavadinRevd.png|380px|thumb|left|The ligand precursor found in amavadin (left), the ligand (center), and H<sub>3</sub> (HIDA, right).]]{{clear-left}} |
[[Image:AmavadinRevd.png|380px|thumb|left|The ligand precursor found in amavadin (left), the ligand (center), and H<sub>3</sub> (HIDA, right).]]{{clear-left}} |
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==Biological function== |
==Biological function== |
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The biological function of amavadin is still unknown, yet it has been thought that it uses H<sub>2</sub>O<sub>2</sub> and acts as a [[peroxidase]] to aid the regeneration of damaged tissues.<ref name="Hub" /> Amavadin may serve as a toxin for protection of the mushroom.<ref>{{cite journal | author = Garner, C.D.; Armstrong, E.M.; Berry, R.E.; Beddoes, R.L.; Collison, D.; Cooney, J.J.A.; Ertok, S.N.; Helliwell, M. | title = Investigations of Amavadin | journal = J. of Inorg. Biochem. | year = 2000 | volume = 80 | pages = 17–20 | doi=10.1016/S0162-0134(00)00034-9}}</ref> |
The biological function of amavadin is still unknown, yet it has been thought that it uses H<sub>2</sub>O<sub>2</sub> and acts as a [[peroxidase]] to aid the regeneration of damaged tissues.<ref name="Hub" /> Amavadin may serve as a toxin for protection of the mushroom.<ref>{{cite journal | author = Garner, C.D.; Armstrong, E.M.; Berry, R.E.; Beddoes, R.L.; Collison, D.; Cooney, J.J.A.; Ertok, S.N.; Helliwell, M. | title = Investigations of Amavadin | journal = J. of Inorg. Biochem. | year = 2000 | volume = 80 | pages = 17–20 | doi=10.1016/S0162-0134(00)00034-9}}</ref> |
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==References== |
==References== |
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{{Poisonous Amanitas}} |
{{Poisonous Amanitas}} |
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[[Category:Vanadium compounds]] |
[[Category:Vanadium compounds]] |
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Revision as of 22:58, 6 January 2011
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| Names | |
|---|---|
| IUPAC name
bis[N-[(1S)-1-(carboxy-κO)ethyl]-N-(hydroxy-κO)-L-alaninato(2-)-.κN,κO]-vanadium
| |
| Identifiers | |
| 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).
| |
Amavadin is a vanadium-containing anion found in three species of poisonous Amanita mushrooms: A. muscaria, A. regalis, and A. velatipes.[1] Amavadin was first isolated and identified in 1972 by Kneifel and Bayer.[2] This anion, which appears as a blue solution, 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 can be used to obtain an NMR spectrum.[3]
Preparation
The formation of amavadin begins with the formation of two tetradentate ligands.[3]
- 2 HON(CH(CH3)CO2H)2 + VO2+ → [V{NO[CH(CH3)CO2]2}2]2− + H2O + 4 H+
Structure and properties
The ligand found in amavadin was first synthesized in 1954.[4] Amavadin contains vanadium(IV). Initially, amavadin was thought to have a vanadyl, VO2+, center. In 1993, it was discovered by crystallographic characterization that amavadin is not a vanadyl ion compound. Instead, it is an octacoordinated vanadium(IV) complex. This complex is bonded to two tetradentate ligands derived from N-hydroxyimino-2,2'-dipropionic acid, H3(HIDPA), ligands.[5] The ligands coordinate through the nitrogen and the three oxygen centers.
Amavadin is a C2-symmetric anion with a 2− 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.
Biological function
The biological function of amavadin is still unknown, yet it has been thought that it uses H2O2 and acts as a peroxidase to aid the regeneration of damaged tissues.[3] Amavadin may serve as a toxin for protection of the mushroom.[6]
References
- ^ a b c d Berry, R.E.; Armstrong, E.M.; Beddoes, R.L.; Collison, D.; Ertok, S.N.; Helliwell, M.; Garner, C.D. (1999). "The Structural Characterization of Amavadin". Angew. Chem. Int. Ed. 38 (6): 795–797. doi:10.1002/(SICI)1521-3773(19990315)38:6<795::AID-ANIE795>3.0.CO;2-7.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Kneifel, H.; Bayer, E. “Stereochemistry and total synthesis of amavadin, the naturally occurring vanadium anion of Amanita muscaria.” J. Am. Chem. Soc. 1986, 108:11, pp. 3075–3077. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/ja00271a043, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1021/ja00271a043instead.. - ^ a b c Hubregtse, T.; Neeleman, E.; Maschmeyer, T.; Sheldon, R.A.;, Hanefeld, U.; Arends, I.W.C.E. (2005). "The first enantioselective synthesis of the amavadin ligand and its complexation to vanadium". J. of Inorg. Biochem. 99: 1264–1267. doi:10.1016/j.jinorgbio.2005.02.004.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Fu, S-C.J.; Birnbaum, S.M.; Greenstein, J.P. (1954). "Influence of Optically Active Acyl Groups on the Enzymatic Hydrolysis of N-Acylated-L-amino Acids". J. Am. Chem. Soc. 76 (23): 6054–6058. doi:10.1021/ja01652a057.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Armstrong, E.M.; Beddoes, R.L.; Calviou, L.J.; Charnock, J.M.; Collison, D.; Ertok, N.; Naismith, J.H.; Garner, C.D. (1993). "The Chemical Nature of Amavadin". J. Am. Chem. Soc. 115 (2): 807–808. doi:10.1021/ja00055a073.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Garner, C.D.; Armstrong, E.M.; Berry, R.E.; Beddoes, R.L.; Collison, D.; Cooney, J.J.A.; Ertok, S.N.; Helliwell, M. (2000). "Investigations of Amavadin". J. of Inorg. Biochem. 80: 17–20. doi:10.1016/S0162-0134(00)00034-9.
{{cite journal}}: CS1 maint: multiple names: authors list (link)
Poisonous Amanita mushrooms | |||||||||||||||||||||||||||||||||||||
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| Subgenus Amanita |
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| Subgenus Amanitina |
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