- 6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline formation by iron mediated dopamine oxidation: A novel route to endogenous neurotoxins under oxidative stress conditions
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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 13C 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.
- Napolitano, Alessandra,Pezzella, Alessandro,Prota, Giuseppe
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p. 2833 - 2836
(2007/10/03)
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