In aqueous buffer, at physiological pHs, 5-hydroxyindole (3) is rapidly oxidised by the H2O2/horseradish peroxidase system to give a complex mixture of oligomeric products, five of which could be isolated after acetylation, and identified as the diacetoxybiindolyls 4 and 5, and the trimers 6, 7 and 8. A similar pattern of products was obtained from the reaction of 3 with other oxidising agents, e.g. potassium ferricyanide, ammonium persulphate and sodium periodate. The Observed reactivity suggests that oxidation of 3 proceeds probably through the intermediacy of the labile quinone Inline 9. This could be trapped In the form of the adduct 12 when 3 was oxidised with o-chloranil in dry ether. © 1988.

A profile of the oxidation chemistry of 5-hydroxyindole under biomimetic conditions / Napolitano, A.; D'Ischia, M.; Prota, G.. - In: TETRAHEDRON. - ISSN 0040-4020. - 44:23(1988), pp. 7265-7270. [10.1016/S0040-4020(01)86098-1]

A profile of the oxidation chemistry of 5-hydroxyindole under biomimetic conditions

Napolitano A.
Primo
;
d'Ischia M.;Prota G.
1988

Abstract

In aqueous buffer, at physiological pHs, 5-hydroxyindole (3) is rapidly oxidised by the H2O2/horseradish peroxidase system to give a complex mixture of oligomeric products, five of which could be isolated after acetylation, and identified as the diacetoxybiindolyls 4 and 5, and the trimers 6, 7 and 8. A similar pattern of products was obtained from the reaction of 3 with other oxidising agents, e.g. potassium ferricyanide, ammonium persulphate and sodium periodate. The Observed reactivity suggests that oxidation of 3 proceeds probably through the intermediacy of the labile quinone Inline 9. This could be trapped In the form of the adduct 12 when 3 was oxidised with o-chloranil in dry ether. © 1988.
1988
A profile of the oxidation chemistry of 5-hydroxyindole under biomimetic conditions / Napolitano, A.; D'Ischia, M.; Prota, G.. - In: TETRAHEDRON. - ISSN 0040-4020. - 44:23(1988), pp. 7265-7270. [10.1016/S0040-4020(01)86098-1]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/906999
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