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唾液酸是一类酸性九碳糖,通过α-糖苷键的方式广泛分布于生物体系内糖缀合物和多聚唾液酸中而发挥着重要的生物学功能。如何有效地构建唾液酸α-糖苷键,合成天然的含有唾液酸的糖缀合物、多聚唾液酸及其衍生物,是糖化学研究的热点和难点。近年来,人们基于唾液酸的结构特点,一方面通过在C2位引入易离去的基团,发展了直接成苷的方法,显著提高成苷的产率;另一方面,通过对C1和C3位引入辅助基团,发展了间接成苷的方法,提高了成苷α-选择性。本文主要从直接成苷和间接成苷两个方面对目前研究的唾液酸糖苷化的化学方法学进行综述。
Sialic acid is a kind of acid non-carbon sugar, which plays an important biological function through the wide distribution of α-glycosidic bond in glycoconjugates and polysialic acids in biological system. How to effectively construct the sialic acid α-glycosidic bond and synthesize the natural sialic acid-containing glycoconjugate, polysialic acid and its derivatives is a hot and difficult point in the research of sugar chemistry. In recent years, people based on the structural characteristics of sialic acid, on the one hand through the introduction of the C2 position easy to leave the group, the development of direct glycosides, significantly increased glycosides yield; the other hand, by C1 and C3 Bit introduction of auxiliary groups, the development of an indirect method of glycoside, increased glycosides α-selectivity. In this paper, the chemical methodology of sialic acid glycosylation has been reviewed from two aspects: direct glycosides and indirect glycosides.