A new insight on the hypochlorous acid scavenging mechanism of tryptamine and tryptophan derivatives.

Abstract:

:The reaction mechanisms of hypochlorous acid (HOCl) with several tryptophan and tryptamine derivatives, previously reported to scavenge this powerful oxidant, was investigated to determine whether ionic or radical pathways were involved. For this purpose, the reaction of tryptamine and tryptophan derivatives with HOCl was optimized and some compounds were isolated by HPLC and their structures assigned. In order to prevent possible radical reaction pathway, experiments have been carried in the presence of the radical trap TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl). The obtained results show that the reaction mechanisms are influenced by the type of structure and that a complex pathway is involved, in which both ionic and radical mechanisms can occur.

journal_name

Bioorg Med Chem Lett

authors

Carvalho LC,Estevão MS,Ferreira LM,Fernandes E,Marques MM

doi

10.1016/j.bmcl.2010.09.067

subject

Has Abstract

pub_date

2010-11-15 00:00:00

pages

6475-8

issue

22

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(10)01368-5

journal_volume

20

pub_type

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