Amavadin

<h2 id="preparation">Preparation</h2>
The formation of amavadin begins with the formation of two tetradentate <a href="/facts/Ligand/6etB3qeW">ligands</a>.<a class="footnote-ref" id="fnref:6" href="#fn:6">6</a>

2 HON(CH(CH3)CO2H)2 + VO2+ → [V{NO[CH(CH3)CO2]2}2]2− + H2O + 4 H+
<h2 id="structure-and-properties">Structure and properties</h2>

The ligand found in amavadin was first synthesized in 1954.<a class="footnote-ref" id="fnref:7" href="#fn:7">7</a> 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 <a href="/facts/Vanadyl_ion/Guma1f7r">vanadyl ion</a> 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.<a class="footnote-ref" id="fnref:8" href="#fn:8">8</a> 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.<a class="footnote-ref" id="fnref:9" href="#fn:9">9</a> There are two possible diastereomers for the ligands, (S,S)-(S,S)-Δ and (S,S)-(S,S)-Λ.

<h2 id="biological-function">Biological function</h2>
The biological function of amavadin is still unknown, yet it has been thought that it uses H2O2 and acts as a <a href="/facts/Peroxidase/pEgHpmCV">peroxidase</a> to aid the regeneration of damaged tissues.<a class="footnote-ref" id="fnref:10" href="#fn:10">10</a> Amavadin may serve as a toxin for protection of the mushroom.<a class="footnote-ref" id="fnref:11" href="#fn:11">11</a>

<h2 id="references">References</h2>

<ol>
<li id="fn:1">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. PMID 29711812. <a href="https://doi.org/10.1002%2F%28SICI%291521-3773%2819990315%2938%3A6%3C795%3A%3AAID-ANIE795%3E3.0.CO%3B2-7" target="_blank">https://doi.org/10.1002%2F%28SICI%291521-3773%2819990315%2938%3A6%3C795%3A%3AAID-ANIE795%3E3.0.CO%3B2-7</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></li>
<li id="fn:2">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. Kneifel, H.; Bayer, E. (1986). "Stereochemistry and total synthesis of amavadin, the naturally occurring vanadium compound of Amanita muscaria". Journal of the American Chemical Society. 108 (11): 3075–3077. doi:10.1021/ja00271a043.. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></li>
<li id="fn:3">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. PMID 29711812. <a href="https://doi.org/10.1002%2F%28SICI%291521-3773%2819990315%2938%3A6%3C795%3A%3AAID-ANIE795%3E3.0.CO%3B2-7" target="_blank">https://doi.org/10.1002%2F%28SICI%291521-3773%2819990315%2938%3A6%3C795%3A%3AAID-ANIE795%3E3.0.CO%3B2-7</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></li>
<li id="fn:4">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. PMID 29711812. <a href="https://doi.org/10.1002%2F%28SICI%291521-3773%2819990315%2938%3A6%3C795%3A%3AAID-ANIE795%3E3.0.CO%3B2-7" target="_blank">https://doi.org/10.1002%2F%28SICI%291521-3773%2819990315%2938%3A6%3C795%3A%3AAID-ANIE795%3E3.0.CO%3B2-7</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></li>
<li id="fn:5">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. Inorg. Biochem. 99 (5): 1264–1267. doi:10.1016/j.jinorgbio.2005.02.004. PMID 15833352. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></li>
<li id="fn:6">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. Inorg. Biochem. 99 (5): 1264–1267. doi:10.1016/j.jinorgbio.2005.02.004. PMID 15833352. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></li>
<li id="fn:7">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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></li>
<li id="fn:8">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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></li>
<li id="fn:9">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. PMID 29711812. <a href="https://doi.org/10.1002%2F%28SICI%291521-3773%2819990315%2938%3A6%3C795%3A%3AAID-ANIE795%3E3.0.CO%3B2-7" target="_blank">https://doi.org/10.1002%2F%28SICI%291521-3773%2819990315%2938%3A6%3C795%3A%3AAID-ANIE795%3E3.0.CO%3B2-7</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></li>
<li id="fn:10">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. Inorg. Biochem. 99 (5): 1264–1267. doi:10.1016/j.jinorgbio.2005.02.004. PMID 15833352. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></li>
<li id="fn:11">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. Inorg. Biochem. 80 (1–2): 17–20. doi:10.1016/S0162-0134(00)00034-9. PMID 10885458. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></li>
</ol>

Amavadin open-in-new

Amavadin