Jacquinet Jean-Claude, Lopin-Bon Chrystel
Institut de Chimie Organique et Analytique, UMR 7311 CNRS et Université d'Orléans, LabEx «SynOrg», Pôle de Chimie, Université d'Orléans, BP 6759, 45067 Orléans Cedex2, France.
Institut de Chimie Organique et Analytique, UMR 7311 CNRS et Université d'Orléans, LabEx «SynOrg», Pôle de Chimie, Université d'Orléans, BP 6759, 45067 Orléans Cedex2, France.
Carbohydr Res. 2015 Jan 30;402:35-43. doi: 10.1016/j.carres.2014.09.007. Epub 2014 Oct 2.
The synthesis of biotinylated conjugates of oligomers of the basic repeating unit of chondroitin sulfate E (CS-E) with the sequence [GlcA-4,6-disulfated GalNAc]n is reported herein for the first time. An efficient and stereocontrolled preparation of di-, tetra-, and hexasaccharide derivatives was achieved using a common key disaccharide intermediate in an iterative way. An unexpected and never reported side reaction on the carbonyl group of the levulinate ester was observed during a coupling reaction. These complex molecules should be useful to study their interactions with various proteins.
本文首次报道了硫酸软骨素E（CS-E）基本重复单元的寡聚物与序列为[GlcA-4,6-二硫酸化GalNAc]n的生物素化缀合物的合成。通过迭代方式使用常见的关键二糖中间体，实现了二糖、四糖和六糖衍生物的高效立体控制制备。在偶联反应过程中观察到乙酰丙酸酯羰基上发生了意外且从未报道过的副反应。这些复杂分子对于研究它们与各种蛋白质的相互作用应该是有用的。
