Department of Biotechnology and Biosciences, University of Milano-Bicocca, P.zza della Scienza 2, 20126 Milano, Italy.
Mini Rev Med Chem. 2011 Jan;11(1):39-54. doi: 10.2174/138955711793564060.
In this article we review our work over the years on carbohydrates and carbohydrate mimetics and their applications in medicinal chemistry. In the first part of the review innovative synthetic methods, such as the chemoselective glycosylation method originally developed by our group and its applications to the synthesis of neoglycoconjugates (neoglycopeptides, oligosaccharide mimetics, neoglycolipids, etc…) will be presented. The high density of functional groups (hydroxyls) on the monosaccharides and the structural role of sugars forming the core of complex glycans in scaffolding and orienting the external sugar units for the interaction with receptors, inspired us and others to use sugars as scaffolds for the construction of pharmacologically active compounds. In the second part of this review, we will present some examples of bioactive and pharmacologically active compounds obtained by decorating monosaccharide scaffolds with pharmacophore groups. Sugar-derived protein ligands were also used as chemical probes to study the interaction of their target with other proteins in the cell. In this context, sugar mimetics and sugar-derived compounds have been employed as tools for exploring biology according to the "chemical genetic" approach.
在本文中，我们回顾了多年来在碳水化合物及其类似物及其在药物化学中的应用方面的工作。在综述的第一部分，将介绍我们小组最初开发的选择性糖基化方法等创新合成方法及其在合成新型糖缀合物（糖肽、寡糖类似物、糖脂等）中的应用。单糖上丰富的功能基团（羟基）以及在形成复杂糖链核心的糖的结构作用，为我们和其他人提供了灵感，使我们将糖作为构建具有药理活性化合物的支架。在综述的第二部分，我们将介绍一些通过在单糖支架上修饰药效团基团获得的生物活性和药理活性化合物的例子。糖衍生的蛋白配体也被用作化学探针来研究其靶标与细胞中其他蛋白的相互作用。在这种情况下，糖类似物和糖衍生的化合物已被用作根据“化学遗传学”方法探索生物学的工具。
