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Computational design of effective, bioinspired HOCl antioxidants: the role of intramolecular Cl+ and H+ shifts

Karton A, O'Reilly RJ, Pattison DI, et al.. Journal of the American Chemical Society, 2012; 134(46):19240-19245.

Laboratory studyOther animals

Design
Laboratory study
What was measured
Computational modelling of the reaction of hypochlorous acid with carnosine and the design of related structures with greater scavenging capacity.

What the authors reported

Modelling suggests the three adjacent functional groups of carnosine (imidazole, carboxylic acid and terminal amine) allow an intramolecular chlorine transfer: two proton shifts coupled with a Cl+ shift convert the kinetically favoured imidazole-chlorinated product into the thermodynamically favoured amine-chlorinated product, trapping the chlorine. Systems sharing these features but with greater HOCl-scavenging capacity were designed.

Limits of this study

Computational study only. Abstract only.

Source

PubMed 23148773 · doi:10.1021/ja309273n

Entry checked against PubMed abstract (E-utilities) on 2026-10-19. The dose shown is the dose the researchers used. It is not a recommendation. How to read this page.