Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec, Canada H3C 3P8.
Beilstein J Org Chem. 2014 Jul 4;10:1524-35. doi: 10.3762/bjoc.10.157. eCollection 2014.
This paper describes the synthesis of three closely related families of mannopyranoside-containing dendrimers for the purpose of studying subtle structural parameters involved in the measurements of multivalent carbohydrate-protein binding interactions. Toward this goal, two trimers 5 and 9, three 9-mers 12, 17, 21, and one 27-mer 23, varying by the number of atoms separating the anomeric and the core carbons, were synthesized using azide-alkyne cycloaddition (CuAAc). Compound 23 was prepared by an efficient convergent strategy. The sugar precursors consisted of either a 2-azidoethyl (3) or a prop-2-ynyl α-D-mannopyranoside (7) derivative. The solvodynamic diameters of 9-mer 12, 17, and 21 were determined by pulsed-field-gradient-stimulated echo (PFG-STE) NMR experiments and were found to be 3.0, 2.5, and 3.4 nm, respectively.
本文描述了三种密切相关的甘露吡喃糖苷包含树状大分子的合成，目的是研究多价糖-蛋白结合相互作用测量中涉及的细微结构参数。为此，使用叠氮-炔环加成（CuAAc）合成了两个三聚体 5 和 9、三个 9- 聚物 12、17、21 和一个 27-聚物 23，它们的原子数不同，分别位于端基碳和核心碳之间。化合物 23 通过有效的收敛策略制备。糖前体由 2-叠氮乙基（3）或丙-2-炔基 α-D-甘露吡喃糖苷（7）衍生物组成。通过脉冲场梯度激发回波（PFG-STE）NMR 实验确定了 9-聚物 12、17 和 21 的溶剂动力学直径，分别为 3.0、2.5 和 3.4nm。
