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Abstract:

Cryptonemia seminervis biosynthesizes a family of d,l-hybrid galactans based on the classical 3-linked β-d-galactopyranosyl→4-linked α-d- and α-l-galactopyranosyl alternating sequence (A-units→B-units) with major amounts of α-d- and α-l-galactose and 3,6-anhydro-d- and l-galactose and lesser percentages of 3,6-anhydro-2-O-methyl-l-galactose, 2-O-methyl-, 4-O-methyl- and 6-O-methylgalactoses. The dispersion of structures in this family is based on five structural factors, namely: (a) the amount and position of substituent groups as sulfate (major), pyruvic acid ketals, methoxyl and glycosyl side-chain (4-O-methyl galactopyranosyl and/or xylosyl); (b) the ratio galactose/3,6-anhydrogalactose in the B-units; (c) the ratio d,l-galactoses and d,l-3,6-anhydrogalactoses also in the B-units, (d) the formation of diads and (e) the sequence of the diads in the linear backbone. Considering these variables it is not unexpected to find in the fractions studied at least 18 structural units producing highly complex structures. Structural studies carried out in two major fractions (S2S-3 and S2S-4) showed that these galactans were formed mainly by β-d-galactopyranosyl 2-sulfate (20 and 11.9 mol %), β-d-galactopyranosyl 2-sulfate 4,6-O-(1′-carboxyethylidene) (8.9 and 6.0 mol %) and β-d-galactopyranosyl 2,6-sulfate (5.4 and 18.6 mol %), together with 3,6-anhydro-α-l-galactopyranosyl (11.4 and 7.3 mol %) and 3,6-anhydro-α-l-galactopyranosyl 2-sulfate (4.9 and 15.4 mol %) and minor quantities of 12-15 other structural units. Preparative alkaline treatment carried out on fraction (S2S-3) produced a quantitative formation of 3,6-anhydro α-l-galactopyranosyl units from precursor units (α-l-galactose 6-sulfate and α-l-galactose 2,6-sulfate). Kinetic studies on this 3,6-anhydro cyclization show a rate constant of 5.2 × 104 s-1 indicating diads of the type G→L6S/2,6S. Data from chemical, spectroscopic and kinetic studies suggest that, in S2S-3, the agaran block in the d,l-hybrid galactan is composed of the following diads: G(6R)→L6S/2,6S and G2S(P)(2,6S)→LA(2S)(2R)(2M) and the carrageenan block of G2S(P)→D(2S)(2,3S)(3S)(3,6S) in a molar ratio of agaran to carrageenan structures of ∼2:1. © 2009 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions
Autor:Zibetti, R.G.M.; Duarte, M.E.R.; Noseda, M.D.; Colodi, F.G.; Ducatti, D.R.B.; Ferreira, L.G.; Cardoso, M.A.; Cerezo, A.S.
Filiación:Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, PO Box: 19046, CEP: 81531-990 Curitiba, Parana, Brazil
Instituto de Ensino Superior Pequeno Príncipe, Curitiba, Paraná, Brazil
Departamento de Química Orgánica, CIHIDECAR-CONICET, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellon 2, 1428 Buenos Aires, Argentina
Palabras clave:Cryptonemia seminervis; Halymeniales; NMR spectroscopy; Polysaccharides; Red seaweed; Sulfated galactans; Cryptonemia seminervis; Halymeniales; NMR spectroscopy; Red seaweed; Sulfated galactans; Biopolymers; Kinetic theory; Nuclear magnetic resonance; Nuclear magnetic resonance spectroscopy; Organic acids; Rate constants; Seaweed; Polysaccharides; acetal; alpha galactosidase; carrageenan; galactan; galactose; monosaccharide; pyranoside; pyruvic acid; sulfate; article; biosynthesis; carbohydrate analysis; carbon nuclear magnetic resonance; chemical reaction; chemical structure; cryptonemia seminervis; cyclization; depolymerization; infrared spectroscopy; kinetics; methylation; nonhuman; priority journal; proton nuclear magnetic resonance; seaweed; Algae, Red; Galactans; Nuclear Magnetic Resonance, Biomolecular; Spectroscopy, Fourier Transform Infrared; Cryptonemia; Cryptonemia seminervis; Halymeniales
Año:2009
Volumen:344
Número:17
Página de inicio:2364
Página de fin:2374
DOI: http://dx.doi.org/10.1016/j.carres.2009.09.003
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:acetal, 105-57-7, 37217-19-9; alpha galactosidase, 9025-35-8; carrageenan, 9000-07-1, 9049-05-2, 9061-82-9, 9064-57-7; galactan, 39300-87-3, 9037-55-2; galactose, 26566-61-0, 50855-33-9, 59-23-4; pyruvic acid, 127-17-3, 19071-34-2, 57-60-3; sulfate, 14808-79-8; Galactans
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v344_n17_p2364_Zibetti

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Citas:

---------- APA ----------
Zibetti, R.G.M., Duarte, M.E.R., Noseda, M.D., Colodi, F.G., Ducatti, D.R.B., Ferreira, L.G., Cardoso, M.A.,..., Cerezo, A.S. (2009) . Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions. Carbohydrate Research, 344(17), 2364-2374.
http://dx.doi.org/10.1016/j.carres.2009.09.003
---------- CHICAGO ----------
Zibetti, R.G.M., Duarte, M.E.R., Noseda, M.D., Colodi, F.G., Ducatti, D.R.B., Ferreira, L.G., et al. "Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions" . Carbohydrate Research 344, no. 17 (2009) : 2364-2374.
http://dx.doi.org/10.1016/j.carres.2009.09.003
---------- MLA ----------
Zibetti, R.G.M., Duarte, M.E.R., Noseda, M.D., Colodi, F.G., Ducatti, D.R.B., Ferreira, L.G., et al. "Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions" . Carbohydrate Research, vol. 344, no. 17, 2009, pp. 2364-2374.
http://dx.doi.org/10.1016/j.carres.2009.09.003
---------- VANCOUVER ----------
Zibetti, R.G.M., Duarte, M.E.R., Noseda, M.D., Colodi, F.G., Ducatti, D.R.B., Ferreira, L.G., et al. Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions. Carbohydr. Res. 2009;344(17):2364-2374.
http://dx.doi.org/10.1016/j.carres.2009.09.003