Oxidation of Primary Alcohol Groups of Polysaccharides with 2,2,6,6-Tetramethyl-1-Piperidine Oxoammonium Ion

2,2,6,6-Tetramethyl-1-Piperidine Oxoammonium Ion에 의한 다당류내 1차 알코올의 특이적 산화

  • Chang, Pahn-Shick (Department of Food Science and Technology, Seoul National Polytechnic University) ;
  • Cho, Gye-Bong (Department of Food Science and Technology, Seoul National Polytechnic University)
  • 장판식 (서울산업대학교 식품공학과) ;
  • 조계봉 (서울산업대학교 식품공학과)
  • Published : 1997.06.01

Abstract

The primary alcohol groups of four kinds of polysaccharides (com starch, rice starch, sweet potato starch, and cellulose), with different structures and water solubilities, were oxidized to carboxyl groups using 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion (TEMPO) at $25^{\circ}C$. The optimum pH, TEMPO content, and NaBr content for the TEMPO/hypobromite-catalyzed oxidation of the polysaccharides were $10.5{\sim}11.0$, 10 mmol/mol primary alcohol, and 0.49 mmol/mol primary alcohol, respectively. The oxidation degree for the primary alcohol group was more than 90% for all four kinds of the polysaccharides. The oxidation process greatly increased the water solubility of the polysaccharides. Water-insoluble polysaccharide such as cellulose became water-soluble to the extent of 8.42% (w/v). And also, the polysaccharides with very low water solubility (less than 0.10% (w/v)) such as com starch, rice starch, and sweet potato starch had high water solubility of approximately 45%(w/v). The gel-forming abilities with calcium ion were determined. The oxidized polysaccharides are new anionic polymers with unique structures that could have application as gums, gels, and films.

Keywords

primary alcohol oxidation;water solubility;gel-forming ability