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Abstract:

The adiabatic conformational surfaces of sixteen 4′,6′,6-trideoxy-α-D-(1→3)-linked disaccharides were obtained using the MM3 force-field at two different dielectric constants. Calculations were carried out on disaccharides with different configurations at C2, C4 and C2′, which are neighbors to the glycosidic linkage, as well as that of the linked carbon (C3). The resulting maps were similar, indicating that the substituents do not play a major role in the conformational features of these disaccharides. However, the preferred minimum conformation and the flexibility were found to be slightly dependant on the configurations of the carbons. Although equatorial bonds and vicinal axial substituents tend to increase the overall flexibility, it was found that these factors can have a cross over effect; i.e., an axial hydroxyl group on C2 may decrease the flexibility if the glycosyl group on C3 is also axial. The relative stabilities of the minimal energy conformations of the 16 compounds also show deviations of the predicted increased stabilities of equatorially substituted compounds over axially substituted ones: these deviations occur mainly for the C2 substituent.

Registro:

Documento: Artículo
Título:Potential energy surfaces of α-(1→3)-linked disaccharides calculated with the MM3 force-field
Autor:Stortz, C.A.; Cerezo, A.S.
Filiación:Depto. de Quimica Organica-CIHIDECAR, Fac. de Ciencias Exact. y Naturales, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina
Palabras clave:Axial; Conformational analysis; Disaccharide maps; Equatorial; MM3; disaccharide; hydroxyl group; article; conformation; dielectric constant; mathematical computing; synthesis
Año:2002
Volumen:21
Número:5
Página de inicio:355
Página de fin:371
DOI: http://dx.doi.org/10.1081/CAR-120014900
Título revista:Journal of Carbohydrate Chemistry
Título revista abreviado:J. Carbohydr. Chem.
ISSN:07328303
CODEN:JCACD
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07328303_v21_n5_p355_Stortz

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Citas:

---------- APA ----------
Stortz, C.A. & Cerezo, A.S. (2002) . Potential energy surfaces of α-(1→3)-linked disaccharides calculated with the MM3 force-field. Journal of Carbohydrate Chemistry, 21(5), 355-371.
http://dx.doi.org/10.1081/CAR-120014900
---------- CHICAGO ----------
Stortz, C.A., Cerezo, A.S. "Potential energy surfaces of α-(1→3)-linked disaccharides calculated with the MM3 force-field" . Journal of Carbohydrate Chemistry 21, no. 5 (2002) : 355-371.
http://dx.doi.org/10.1081/CAR-120014900
---------- MLA ----------
Stortz, C.A., Cerezo, A.S. "Potential energy surfaces of α-(1→3)-linked disaccharides calculated with the MM3 force-field" . Journal of Carbohydrate Chemistry, vol. 21, no. 5, 2002, pp. 355-371.
http://dx.doi.org/10.1081/CAR-120014900
---------- VANCOUVER ----------
Stortz, C.A., Cerezo, A.S. Potential energy surfaces of α-(1→3)-linked disaccharides calculated with the MM3 force-field. J. Carbohydr. Chem. 2002;21(5):355-371.
http://dx.doi.org/10.1081/CAR-120014900