Partial and total C-6 oxidation of gelling carrageenans. Modulationof the antiviral activity with the anionic character

COSENZA, V.A.; NAVARRO, D.A.; PUJOL, C.A.; DAMONTE, E.B.; STORTZ, C.A.

CARBOHYDRATE POLYMERS

ELSEVIER SCI LTD

Lugar: Amsterdam; Año: 2015

0144-8617

The optimal conditions for the full C-6 oxidation of kappa- and iota-carrageenans using TEMPO in the presence of sodium hypochlorite and sodium bromide were assessed. The fully oxidized products were characterized by NMR spectroscopy. Partially oxidized products werealso obtained and analyzed by chemical and spectroscopical methods. Theantiviral activity of carrageenans against HSV-1 and HSV-2 determined by plaque reduction assay was not largely affected by full oxidation of the polysaccharides, but an increase in activity was detected by partial oxidation. A specific overoxidation on C-2 of the 3,6-anhydrogalactose moiety of kappa-carrageenan was identified, solved experimentally and rationalized through the application of molecular modeling.