Production and characterization of new families of polyglucuronic acids from TEMPO-NaOCl oxidation of curdlan

Int J Biol Macromol. 2009 Dec 1;45(5):458-62. doi: 10.1016/j.ijbiomac.2009.08.005. Epub 2009 Aug 28.

Abstract

Curdlan from Agrobacterium sp. was oxidized using 2,2,6,6,-tetramethylpiperidine-1-oxyl radical (TEMPO)-NaBr-NaClO systems at pH 11. The effects of oxidation conditions on degrees of oxidation and polymerization of the products obtained were studied using SEC-MALLS, NMR and IR analyses. Different families of water-soluble beta-(1,3)-polyglucuronic and beta-(1,3)-polyglucoglucuronic acid sodium salts were quantitatively generated with a yield of 80% and without significant loss of their molecular weights. Given that beta-(1,3)-polyglucuronic acids prepared from the regioselective oxidation of curdlan by the TEMPO-NaBr-NaClO systems regularly consist of the glucuronic acid repeating unit; they may open new biotechnological fields for the utilizations of water soluble forms of curdlan.

MeSH terms

  • Carbohydrates / chemistry
  • Cyclic N-Oxides / chemistry
  • Cyclic N-Oxides / pharmacology*
  • Electrochemistry / methods
  • Glucuronates / chemistry*
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy / methods
  • Models, Chemical
  • Molecular Weight
  • Oxygen / chemistry
  • Rhizobium / metabolism
  • Sodium Hypochlorite / chemistry*
  • Spectrophotometry, Infrared / methods
  • Spectroscopy, Fourier Transform Infrared
  • Water / chemistry
  • beta-Glucans / chemistry*

Substances

  • Carbohydrates
  • Cyclic N-Oxides
  • Glucuronates
  • beta-Glucans
  • Water
  • curdlan
  • Sodium Hypochlorite
  • Oxygen
  • TEMPO