Aerobic oxidation of dopamine mediated by iron ions gives 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (2) and 3,4-dihydroxybenzaldehyde (4) in yields up to 10% and 15%, respectively. Based on C-13 labelling experiments, a reaction mechanism is proposed involving oxidative fission of the dopamine side chain to give 4 and formaldehyde, the latter giving 2 by Pictet-Spengler condensation with dopamine. This provides a novel route to endogenous generation of neurotoxic isoquinoline alkaloids under oxidative stress conditions
6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline formation by iron mediated dopamine oxidation: a novel route to endogenous neurotoxins under oxidative stress conditions / Napolitano, Alessandra; Pezzella, Alessandro; G. P. R. O. T., A.. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 40:14(1999), pp. 2833-2836. [10.1016/S0040-4039(99)00272-5]
6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline formation by iron mediated dopamine oxidation: a novel route to endogenous neurotoxins under oxidative stress conditions.
NAPOLITANO, ALESSANDRA;PEZZELLA, ALESSANDRO;
1999
Abstract
Aerobic oxidation of dopamine mediated by iron ions gives 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (2) and 3,4-dihydroxybenzaldehyde (4) in yields up to 10% and 15%, respectively. Based on C-13 labelling experiments, a reaction mechanism is proposed involving oxidative fission of the dopamine side chain to give 4 and formaldehyde, the latter giving 2 by Pictet-Spengler condensation with dopamine. This provides a novel route to endogenous generation of neurotoxic isoquinoline alkaloids under oxidative stress conditionsI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
