Chloride ion and N-acyl group react to chloramide

Stable Identifier
R-HSA-6789185
Type
Reaction [transition]
Species
Homo sapiens
Compartment
phagocytic vesicle lumen
ReviewStatus
5/5
Locations in the PathwayBrowser
Expand all
General
SVG | 
PNG
Low
Medium
High
 | PPTX  | SBGN
Chloride ion and N-acyl group react to chloramide
Click the image above or here to open this reaction in the Pathway Browser
The layout of this reaction may differ from that in the pathway view due to the constraints in pathway layout
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
Participants
Input
Output
Entity On Other Cell
Participates
as an event of
Authored
Shamovsky, V  (2018-10-23)
Reviewed
Nüsse, O  (2018-11-07)
Created
Shamovsky, V  (2015-07-29)
Cite Us!