Wessel H P, Bartsch S
F. Hoffmann-La Roche Ltd, Pharma Division, Basel, Switzerland.
Carbohydr Res. 1995 Sep 8;274:1-9. doi: 10.1016/0008-6215(95)00131-c.
Triggered by findings on heparin-like disaccharides, the conformation of sulfated glucopyranosides was investigated. Sodium (methyl 2,3,4-tri-O-sulfonato-beta-D-glucopyranosid)uronate tetrasodium salt is in a conformational equilibrium, to which a non-chair conformation contributes. The same is true for methyl (methyl 2,3,4-tri-O-sulfonato-beta-D-glucopyranosid)uronate trisodium salt, methyl 2,3,4,6-tetra-O-sulfonato-beta-D-glucopyranoside tetrasodium salt, and octa-O-sulfonato-beta, beta-trehalose octasodium salt, with less obvious non-chair contributions. The effect is charge related. The conformational effect, which does not occur in analogous alpha-D-glucopyranoside derivatives, is discussed in terms of the anomeric effect.
受类肝素二糖研究结果的启发，对硫酸化吡喃葡萄糖苷的构象进行了研究。（甲基2,3,4-三-O-磺基-β-D-吡喃葡萄糖苷）糖醛酸钠四钠盐处于构象平衡状态，其中非椅式构象也有贡献。（甲基2,3,4-三-O-磺基-β-D-吡喃葡萄糖苷）糖醛酸甲酯三钠盐、2,3,4,6-四-O-磺基-β-D-吡喃葡萄糖苷四钠盐和八-O-磺基-β,β-海藻糖八钠盐也是如此，只是非椅式构象的贡献不太明显。这种效应与电荷有关。根据端基异构效应讨论了在类似的α-D-吡喃葡萄糖苷衍生物中未出现的构象效应。
