6-oxychitins, novel hyaluronan-like regiospecifically carboxylated chitins

Crustacean chitins and fungal chitin-glucan complexes are subjected to regiospecific oxidation at C-6 with NaOCl in the presence of Tempo(R) and NaBr at 25 degrees C in aqueous solution. The resulting products have anionic character and are fully soluble over the entire pH range; they lend themselves to metal chelation, polyelectrolyte complex formation with a number of biopolymers including chitosan, and to microsphere and bead formation. 6-Oxychitin coagulates papain, lysozyme and other hydrolases active on chitosans. 6-Oxychitins of fungal and animal origins, in the form of free acids, salts and esters, might find use as surrogates of hyaluronans and of bacterial antigens in medical and health care products. (C) 1999 Elsevier Science Ltd. All rights reserved.