Oxidation of Primary Alcohol Groups of Naturally Occurring Polysaccharides with 2,2,6,6-Tetramethyl-1-Piperidine Oxoammonium Ion
- 1 September 1996
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 15 (7) , 819-830
- https://doi.org/10.1080/07328309608005694
Abstract
The primary alcohol groups of ten polysaccharides, with widely different structures and water solubilities, were oxidized to carboxyl groups using 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion (TEMPO) at pH 10.8 and 0°C. The yield and selectivity for the primary alcohol group were high for all ten of the polysaccharides. The oxidation greatly increased the water-solubility of the polysaccharides. Water-insoluble polysaccharides such as amylose, cellulose, and chitin became water-soluble to the extent of approximately 10% (w/v). The water-soluble polysaccharides had their degree of solubility doubled or tripled. The specific optical rotation, viscosity, and gelling properties 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
This publication has 11 references indexed in Scilit:
- Highly selective nitroxyl radical-mediated oxidation of primary alcohol groups in water-soluble glucansPublished by Elsevier ,2000
- Highly selective tempo mediated oxidation of primary alcohol groups in polysaccharidesRecueil des Travaux Chimiques des Pays-Bas, 1994
- Fast and selective oxidation of primary alcohols to aldehydes or to carboxylic acids and of secondary alcohols to ketones mediated by oxoammonium salts under two-phase conditionsThe Journal of Organic Chemistry, 1987
- The formation of α-d-(1→3) branch linkages by an exocellular glucansucrase from Leuconostoc mesenteroides NRRL B-742Carbohydrate Research, 1983
- Isolation and partial characterization of an extracellular glucansucrase from Leuconostoc mesenteroides NRRL B-1355 that synthesizes an alternating (1→6), (1→3)-α-d-glucanCarbohydrate Research, 1982
- Structural analysis of leuconostoc dextrans containing 3-O-α-d-glucosylated α-d-glucosyl residues in both linear-chain and branch-point positions, or only in branch-point positions, by methylation and by 13C-N.M.R. spectroscopyCarbohydrate Research, 1979
- Methylation structural analysis of unusual dextrans by combined gas-liquid chromatography-mass spectrometryCarbohydrate Research, 1979
- Pullulan, ein extracelluläres Glucan von Pullularia pullulansBiochimica et Biophysica Acta, 1959
- Heterogeneity in dextran preparationsArchives of Biochemistry and Biophysics, 1955
- Properties of the Fractions and Linear Subfractions from Various StarchesJournal of the American Chemical Society, 1949