Chloride ion and N-acyl group react to chloramide

Stable Identifier
Reaction [transition]
Homo sapiens
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UV-visible (220-340 nm) and EPR spectroscopy monitoring of reaction of HOCl/ClO- with amides, sugars, polysaccharides, and hyaluronic acid indicate that HOCl/ClO- reacts preferentially with N-acetyl groups (Hawkins CL & Davies MJ 1998; Rees MD et al. 2003). This reaction is believed to give rise to transient chloramide (R-NCl-C(O)-R') species, which decompose rapidly to give radicals. A polymer fragmentation is thought to involve one-electron reduction of the chloramides to yield polymer-derived amidyl radicals, which subsequently undergo intramolecular hydrogen atom abstraction reactions to give carbon-centered radicals (Hawkins CL & Davies MJ 1998; Rees MD et al. 2003). The latter undergo fragmentation reactions in a site-specific manner.

The basic structure of bacterial peptidoglycan (PGN) contains a carbohydrate backbone of alternating units of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc), which can be a target for HOCl -mediated oxidation (van Heijenoort J et al. 2001; Davies MJ 2011).

Literature References
PubMed ID Title Journal Year
9450756 Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils

Eiserich, JP, Freeman, BA, Jones, AD, Cross, CE, Hristova, M, van der Vliet, A, Halliwell, B

Nature 1998
9641257 Degradation of hyaluronic acid, poly- and monosaccharides, and model compounds by hypochlorite: evidence for radical intermediates and fragmentation

Davies, MJ, Hawkins, CL

Free Radic. Biol. Med. 1998
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