Studies on the cationization of agarose |
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Authors: | Prado Héctor J Matulewicz María C Bonelli Pablo R Cukierman Ana L |
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Institution: | aDepartamento de Química Orgánica—CIHIDECAR-(CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina;bPINMATE-Departamento de Industrias, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina;cCátedra de Farmacotecnia II, Departamento de Tecnología Farmacéutica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, C1113AAD Buenos Aires, Argentina |
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Abstract: | Cationized agaroses with different degrees of substitution (0.04–0.77) were synthesized, employing 3-chloro-2-hydroxypropyltrimethylammonium chloride (CHPTAC). The influence of different reaction parameters on the substitution degree and molecular weight was evaluated. The investigated parameters were concentration of reagents, temperature, time, and addition of NaBH4. The products were characterized by means of scanning electronic microscopy, infrared spectroscopy, viscosimetry, and NMR spectroscopy. Methanolysis products were studied by electrospray ionization mass spectrometry. The higher the concentration of CHPTAC employed, a higher degree of substitution was obtained, if the optimum concentration of NaOH in each case was employed. Insufficient quantities of NaOH reduced epoxide formation and the reacting alkoxides of the polysaccharide, whereas an excess of NaOH favored degradation of the epoxide and decrease in the molecular weight of the product. A reaction time of 2 h was sufficient to obtain products with the maximum degree of substitution for each case. The addition of NaBH4 gave products with a slightly higher molecular weight, but the extra cost involved should not justify its use for large-scale application. |
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Keywords: | Agarose Cationization Cationic polysaccharide 3-Chloro-2-hydroxypropyltrimethylammonium chloride |
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