Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives
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 car...
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2002
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n21-23_p2311_Stortz http://hdl.handle.net/20.500.12110/paper_00086215_v337_n21-23_p2311_Stortz |
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paper:paper_00086215_v337_n21-23_p2311_Stortz2023-06-08T14:32:43Z Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives Stortz, Carlos Arturo 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 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. Fil:Stortz, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2002 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n21-23_p2311_Stortz http://hdl.handle.net/20.500.12110/paper_00086215_v337_n21-23_p2311_Stortz |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Stortz, Carlos Arturo Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives |
| topic_facet |
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 |
| description |
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. |
| author |
Stortz, Carlos Arturo |
| author_facet |
Stortz, Carlos Arturo |
| author_sort |
Stortz, Carlos Arturo |
| title |
Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives |
| title_short |
Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives |
| title_full |
Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives |
| title_fullStr |
Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives |
| title_full_unstemmed |
Potential energy surfaces of carrageenan models: Carrabiose, β-(1→4)-linked D-galactobiose, and their sulfated derivatives |
| title_sort |
potential energy surfaces of carrageenan models: carrabiose, β-(1→4)-linked d-galactobiose, and their sulfated derivatives |
| publishDate |
2002 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n21-23_p2311_Stortz http://hdl.handle.net/20.500.12110/paper_00086215_v337_n21-23_p2311_Stortz |
| work_keys_str_mv |
AT stortzcarlosarturo potentialenergysurfacesofcarrageenanmodelscarrabioseb14linkeddgalactobioseandtheirsulfatedderivatives |
| _version_ |
1768546657377452032 |