title: Studies on the cationization of agarose.
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 NaBH(4). 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 2h was sufficient to obtain products with the maximum degree of substitution for each case. The addition of NaBH(4) gave products with a slightly higher molecular weight, but the extra cost involved should not justify its use for large-scale application.
authors.affiliation: Departamento de Química Orgánica-CIHIDECAR-(CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
authors.forename: Héctor J
authors.initials: HJ
authors.lastname: Prado
authors.forename: María C
authors.initials: MC
authors.lastname: Matulewicz
authors.forename: Pablo R
authors.initials: PR
authors.lastname: Bonelli
authors.forename: Ana L
authors.initials: AL
authors.lastname: Cukierman
mesh_terms: D001894:Borohydrides / Q000737:chemistry; D002412:Cations / Q000737:chemistry; D007259:Infrared Rays; D009682:Magnetic Resonance Spectroscopy; D008855:Microscopy, Electron, Scanning; D020005:Propanols / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012685:Sepharose / Q000138:chemical synthesis* / Q000737:chemistry / Q000648:ultrastructure*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D014783:Viscosity
chemical_list: D001894:Borohydrides; D002412:Cations; D020005:Propanols; D000644:Quaternary Ammonium Compounds; C025364:sodium borohydride; D012685:Sepharose; C496948:(3-chloro-2-hydroxypropyl)trimethylammonium chloride