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Abstract:

The adiabatic conformational surfaces of several β-linked disaccharides, which correspond to the repeating structures of carrageenans, were calculated using the MM3 force-field. The studies were carried out on the disaccharide β-D-Galp-(1→4)-α-D-Galp and eight sulfated derivatives, as well as on carrabiose (β-D-Galp-(1→4)-3,6-An-α-D-Galp) and five sulfated derivatives. The presence of 3,6-anhydrogalactose does not change the main features of the maps, although it increases the flexibility of the glycosidic linkage. Sulfation neither produces a striking effect on the map shape, nor a shift on the global minimum, which always remains with ψ (θC-1′-O-4-C-4-C-5) in trans orientation, and φ (θO-5′-C-1′-O-4-C-4) with a value close to -80°. This effect differs from that occurring on the α linkage of equivalent disaccharides, for which the sulfation pattern on the β-galactose unit shifts the global minima to different positions. A reduction in the flexibility (originated in a deepening of the global minimum well) is observed by sulfation on position 2 of the β-D-galactose unit, and by sulfation of position 6 of the α-D-galactose unit (when the β-D-galactose unit is 4-sulfated). Within the compounds containing 3,6-anhydrogalactose, the effect of sulfation is even less noticeable. The calculated low-energy regions on carrabiose derivatives agree with X-ray diffraction data on carrageenan fibers and on peracetylated carrabiose dimethyl acetal, and with NOE calculations carried out on κ-carrabiose. © 2002 Elsevier Science Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives
Autor:Stortz, C.A.
Filiación:Departamento De Química Orgánica-CIHIDECAR, Facultad De Ciencias Exactas Y Naturales, UBA, Pab. 2 Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Carrabiose; Carrageenans; Conformational analysis; Disaccharide maps; MM3; Derivatives; Potential energy; Reduction; X ray diffraction; Sulfation; Carbohydrates; 3,6 anhydrogalactose; beta dextro galactose; carbohydrate derivative; carrabiose; carrageenan; disaccharide; galactobiose; unclassified drug; article; calculation; conformation; energy; priority journal; reduction; sulfation; X ray diffraction; Carbohydrate Conformation; Carrageenan; Disaccharides; Models, Molecular; Sulfuric Acid Esters
Año:2002
Volumen:337
Número:21-23
Página de inicio:2311
Página de fin:2323
DOI: http://dx.doi.org/10.1016/S0008-6215(02)00173-8
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:6-O-galactopyranosylgalactose, 5077-31-6; carrabiose, 19253-99-7; Carrageenan, 9000-07-1; Disaccharides; Sulfuric Acid Esters
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n21-23_p2311_Stortz

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Citas:

---------- APA ----------
(2002) . Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives. Carbohydrate Research, 337(21-23), 2311-2323.
http://dx.doi.org/10.1016/S0008-6215(02)00173-8
---------- CHICAGO ----------
Stortz, C.A. "Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives" . Carbohydrate Research 337, no. 21-23 (2002) : 2311-2323.
http://dx.doi.org/10.1016/S0008-6215(02)00173-8
---------- MLA ----------
Stortz, C.A. "Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives" . Carbohydrate Research, vol. 337, no. 21-23, 2002, pp. 2311-2323.
http://dx.doi.org/10.1016/S0008-6215(02)00173-8
---------- VANCOUVER ----------
Stortz, C.A. Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives. Carbohydr. Res. 2002;337(21-23):2311-2323.
http://dx.doi.org/10.1016/S0008-6215(02)00173-8