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
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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
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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
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Volumen: | 337
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Número: | 21-23
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Página de inicio: | 2311
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Página de fin: | 2323
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DOI: |
http://dx.doi.org/10.1016/S0008-6215(02)00173-8 |
Título revista: | Carbohydrate Research
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Título revista abreviado: | Carbohydr. Res.
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ISSN: | 00086215
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CODEN: | CRBRA
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CAS: | 6-O-galactopyranosylgalactose, 5077-31-6; carrabiose, 19253-99-7; Carrageenan, 9000-07-1; Disaccharides; Sulfuric Acid Esters
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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