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Abstract:

The cyclization reaction (formation of 3,6-anhydro-α-d-galactose units from α-d-galactose 6-sulfate) of carrageenans follows a pseudo first-order kinetics, being 20-60 times faster for carrageenans of the kappa-family than for those of the lambda-family. In lambda-carrageenans the clustering of the sulfate groups around the hydroxyl on C-3 of the α-unit shields it from polarization or ionization, reducing the cyclization reaction rate. Furthermore, molecular models of lambda-carrageenans suggest an adequate geometry for the interaction between the hydroxyl group on C-3 of the α-unit and the sulfate group on C-2 of the β-unit. These observations also explain the lack of cyclized derivatives of lambda-carrageenans in nature. The ease with which the cyclization reaction occurs for carrageenans of the kappa-family indicates that the alkaline treatments used industrially could be carried out under milder conditions, giving products of high gel strength. © 1993.

Registro:

Documento: Artículo
Título:Alkali-modification of carrageenans: mechanism and kinetics in the kappa/iota-, mu/nu- and lambda-series
Autor:Ciancia, M.; Noseda, M.D.; Matulewicz, M.C.; Cerezo, A.S.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Departamento de Bioquímica, Setor de Ciencias Biológicas, Universidade Federal do Paraná, Curitiba, Brazil
Palabras clave:Chemical modification; Gelation; Molecular structure; Plants (botany); Reaction kinetics; Synthesis (chemical); Alkali modification; Anhydrogalactose; Carrageenans; Cyclization; Cystocarpic plants; Galactose sulfate; Kappa series; Lambda series; Tetrasporic plants; Sugars
Año:1993
Volumen:20
Número:2
Página de inicio:95
Página de fin:98
DOI: http://dx.doi.org/10.1016/0144-8617(93)90083-G
Título revista:Carbohydrate Polymers
Título revista abreviado:Carbohydr Polym
ISSN:01448617
CODEN:CAPOD
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01448617_v20_n2_p95_Ciancia

Referencias:

  • Ciancia, M., Matulewicz, M.C., Finch, P. & Cerezo, A.S. (in press). Determination of the structures of cystocarpic carrageenans from Gigartina skottsbergii by methylation analysis and n.m.r. spectroscopy. Carbohydr. Res; Fransson, Maemström, Söjberg, Huckerby, Periodate oxidation and alkaline degradation of heparin related glycans (1980) Carbohydr. Res., 80, pp. 131-145
  • Glicksman, (1983) Food Hydrocolloids, 2, p. 83. , M. Glicksman, CRC Press, Boca Raton, Florida
  • Matulewicz, Ciancia, Noseda, Cerezo, Carrageenan systems from tetrasporic and cystocarpic stages of Gigartina skottsbergii (1989) Phytochemistry, 28, pp. 2937-2941
  • Matulewicz, Ciancia, Noseda, Cerezo, Methylation analysis of carrageenans from tetrasporic and cystocarpic stages of Gigartina skottsbergii (1990) Phytochemistry, 29, pp. 3407-3410
  • Noseda, M.D. & Cerezo, A.S. (in press). Room temperature, low field 13 C n.m.r. spectra of degraded carrageenans. Part III: Autohydrolysis of a lambda carrageenan and of its alkali-treated derivative. Int. J. Biol. Macromol; Painter, (1983) The Polysaccharides, 2, p. 213. , G.O. Aspinall, Academic Press, London
  • Percival, Carbohydrate sulfates (1949) Quart. Rev. (Lond.), 3, pp. 369-384
  • Rees, Estimation of the relative amounts of isomeric sulfate esters in some sulfated polysaccharides (1961) Journal of the Chemical Society (Resumed), pp. 5168-5171
  • Turvey, Sulfates of the simple sugars (1965) Adv. Carbohydr. Chem., 20, pp. 183-218
  • Wong, Craigie, Sulfohydrolase activity and carrageenan biosynthesis in Chondrus crispus (Rhodophyceae) (1978) PLANT PHYSIOLOGY, 61, pp. 663-666
  • Yaphe, Colorimetric determination of 3,6-anhydrogalactose and galactose in marine algal polysaccharides (1960) Anal. Chem., 32, pp. 1327-1330

Citas:

---------- APA ----------
Ciancia, M., Noseda, M.D., Matulewicz, M.C. & Cerezo, A.S. (1993) . Alkali-modification of carrageenans: mechanism and kinetics in the kappa/iota-, mu/nu- and lambda-series. Carbohydrate Polymers, 20(2), 95-98.
http://dx.doi.org/10.1016/0144-8617(93)90083-G
---------- CHICAGO ----------
Ciancia, M., Noseda, M.D., Matulewicz, M.C., Cerezo, A.S. "Alkali-modification of carrageenans: mechanism and kinetics in the kappa/iota-, mu/nu- and lambda-series" . Carbohydrate Polymers 20, no. 2 (1993) : 95-98.
http://dx.doi.org/10.1016/0144-8617(93)90083-G
---------- MLA ----------
Ciancia, M., Noseda, M.D., Matulewicz, M.C., Cerezo, A.S. "Alkali-modification of carrageenans: mechanism and kinetics in the kappa/iota-, mu/nu- and lambda-series" . Carbohydrate Polymers, vol. 20, no. 2, 1993, pp. 95-98.
http://dx.doi.org/10.1016/0144-8617(93)90083-G
---------- VANCOUVER ----------
Ciancia, M., Noseda, M.D., Matulewicz, M.C., Cerezo, A.S. Alkali-modification of carrageenans: mechanism and kinetics in the kappa/iota-, mu/nu- and lambda-series. Carbohydr Polym. 1993;20(2):95-98.
http://dx.doi.org/10.1016/0144-8617(93)90083-G