The action of hypochlorous acid on polymeric components of cartilage.
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.
Schiller
J
J
Institut für Medizinische Physik und Biophysik, Universität Leipzig, Germany.
Arnhold
J
J
Gründer
W
W
Arnold
K
K
D000116:Acetylgalactosamine / Q000737:chemistry; D000117:Acetylglucosamine / Q000737:chemistry; D000818:Animals; D002356:Cartilage / Q000737:chemistry*; D002417:Cattle; D002809:Chondroitin Sulfates / Q000737:chemistry; D005260:Female; D006801:Humans; D006820:Hyaluronic Acid / Q000737:chemistry; D006997:Hypochlorous Acid / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011108:Polymers / Q000737:chemistry*; D011247:Pregnancy; D014132:Trachea / Q000737:chemistry; D014470:Umbilical Cord / Q000737:chemistry
D007202:Indicators and Reagents; D011108:Polymers; D006997:Hypochlorous Acid; D006820:Hyaluronic Acid; D002809:Chondroitin Sulfates; D000116:Acetylgalactosamine; D000117:Acetylglucosamine