HOCl-induced glycosaminoglycan fragmentation

Stable Identifier
Reaction [omitted]
Homo sapiens
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UV-visible (220-340 nm) and EPR spectroscopy monitoring of reaction of hypochlorite HOCl/ClO- with amides, sugars, polysaccharides, and hyaluronic acid 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-centred 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).

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