Regioselective one-pot protection of carbohydrates
Regioselective one-pot protection of carbohydrates
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DOI：
10.1038/nature05730
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发表时间：
2007-04-19
期刊：
影响因子：
64.8
通讯作者：
Hung, Shang-Cheng
中科院分区：
文献类型：
--
作者：
Wang, Cheng-Chung;Lee, Jinq-Chyi;Hung, Shang-Cheng
碳水化合物参与广泛的生物过程(1-4)。这些结构多样的化合物比其他生物聚合物更复杂，在自然界中经常以非均相混合物的形式存在。碳水化合物的化学合成是获得纯寡糖的一种方法，但它受到与多羟基的区域选择性保护有关的困难和与糖苷键的立体选择性组装有关的挑战的阻碍(5-14)。在这里，我们描述了一种组合的，高度区域选择性的方法，可以用来保护单糖的单个羟基。这种方法可用于在单个反应容器中安装正交保护基团图案(一锅反应)，从而消除了对中间体进行耗时的分离和纯化的需要。从D-葡萄糖开始，已经有效地制备了数百个构建块，这些构建块的迭代耦合使我们能够组装β-1，6-葡聚糖和基于流感病毒结合三糖的寡糖库。
Carbohydrates are involved in a wide range of biological processes(1-4). These structurally diverse compounds are more complex than other biological polymers, and are often present as heterogeneous mixtures in nature. The chemical synthesis of carbohydrates is one way to obtain pure oligosaccharides, but it is hampered by difficulties associated with the regioselective protection of polyhydroxyls and challenges related to the stereoselective assembly of glycosidic linkages(5-14). Here we describe a combinatorial, and highly-regioselective, method that can be used to protect individual hydroxy groups of a monosaccharide. This approach can be used to install an orthogonal protecting group pattern in a single reaction vessel (a 'one-pot' reaction), which removes the need to carry out the time-consuming isolation and purification of intermediates. Hundreds of building blocks have been efficiently prepared starting from D-glucose, and the iterative coupling of these building blocks enabled us to assemble beta-1,6-glucans and a library of oligosaccharides based on the influenza-virus binding trisaccharide.