Related Experiment Video
Updated: Aug 18, 2026

Mechanical Stimulation of Chondrocyte-agarose Hydrogels
Published on: October 27, 2012
The action of hypochlorous acid on polymeric components of cartilage
J Schiller1, J Arnhold, W Gründer
1Institut für Medizinische Physik und Biophysik, Universität Leipzig, Germany.
Abstract:
The action of sodium hypochlorite on N-acetylglucosamine, N-acetylgalactosamine, chondroitinsulfate and hyaluronic acid was studied by 1H-nuclear magnetic resonance (1H-NMR) in order to model some aspects of degradation processes caused by neutrophils on carbohydrate polymers of cartilage in rheumatoid arthritis. N-Acetyl side groups of carbohydrate monomers and chondroitinsulfate yield a resonance at 2.01-2.04 ppm in proton NMR-spectra. This resonance is observed in hyaluronic acid solutions only after a prolonged incubation to yield shorter polymeric chains. Sodium hypochlorite causes a continuous decrease of the line for N-acetyl groups. Two new resonances appear in the 1H-NMR spectra. An intermediate product, assumed as a chlorinated product of N-acetyl side chains, shows a chemical shift of about 2.35 ppm. This intermediate is hydrolyzed to a carbohydrate ring and acetate (1.90 ppm). Sodium hypochlorite acts in all systems investigated mainly on N-acetyl groups. Only small effects on the carbohydrate ring were found under our experimental conditions.
Related Concept Videos
Polyprotic Acids
Carboxylic Acids to Acid Chlorides
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
Preparation of Acid Anhydrides
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Growth of Cartilage and Bone Tissue

