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Abstract:

The adiabatic conformational surfaces of neocarrabiose (3,6-An-α-D-Galp-(1→3)-β-D-Galp) and of nine sulfated and/or pyruvylated derivatives were obtained using the MM3 force-field. These maps indicate greater flexibility of the glycosidic linkage than found for similar compounds that are based on α-D-galactose instead of 3,6-anhydrogalactose units. Sulfation of the β-D-galactose unit on position 2 shifts the global minimum to negative ψH (θCl'-O3-C3-H3) angles, whereas sulfation at either position 4 of the same unit or at position 2 of the 3,6-anhydro-α-D-galactose unit has less effect. The results are consistent with the X-ray diffraction data on crystalline neocarrabiose and carrageenan fibers. Free energy calculations show that entropy is not uniformly distributed among confomers.

Registro:

Documento: Artículo
Título:Conformational analysis of neocarrabiose and its sulfated and/or pyruvylated derivatives using the MM3 force-field
Autor:Stortz, C.A.; Cerezo, A.S.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina
Año:2000
Volumen:19
Número:9
Página de inicio:1115
Página de fin:1130
DOI: http://dx.doi.org/10.1080/07328300008544138
Título revista:Journal of Carbohydrate Chemistry
Título revista abreviado:J. Carbohydr. Chem.
ISSN:07328303
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07328303_v19_n9_p1115_Stortz

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Citas:

---------- APA ----------
Stortz, C.A. & Cerezo, A.S. (2000) . Conformational analysis of neocarrabiose and its sulfated and/or pyruvylated derivatives using the MM3 force-field. Journal of Carbohydrate Chemistry, 19(9), 1115-1130.
http://dx.doi.org/10.1080/07328300008544138
---------- CHICAGO ----------
Stortz, C.A., Cerezo, A.S. "Conformational analysis of neocarrabiose and its sulfated and/or pyruvylated derivatives using the MM3 force-field" . Journal of Carbohydrate Chemistry 19, no. 9 (2000) : 1115-1130.
http://dx.doi.org/10.1080/07328300008544138
---------- MLA ----------
Stortz, C.A., Cerezo, A.S. "Conformational analysis of neocarrabiose and its sulfated and/or pyruvylated derivatives using the MM3 force-field" . Journal of Carbohydrate Chemistry, vol. 19, no. 9, 2000, pp. 1115-1130.
http://dx.doi.org/10.1080/07328300008544138
---------- VANCOUVER ----------
Stortz, C.A., Cerezo, A.S. Conformational analysis of neocarrabiose and its sulfated and/or pyruvylated derivatives using the MM3 force-field. J. Carbohydr. Chem. 2000;19(9):1115-1130.
http://dx.doi.org/10.1080/07328300008544138