Advanced Chemical Methods for Stereoselective Sialylation and Their Applications in Sialoglycan Syntheses
Advanced Chemical Methods for Stereoselective Sialylation and Their Applications in Sialoglycan Syntheses
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DOI：
10.1002/tcr.202100080
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发表时间：
2021-05
期刊：
影响因子：
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通讯作者：
Amol M. Vibhute;N. Komura;Hide-Nori Tanaka;A. Imamura;H. Ando
中科院分区：
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作者：
Amol M. Vibhute;N. Komura;Hide-Nori Tanaka;A. Imamura;H. Ando
唾液酸是细胞表面聚糖的重要组成部分，负责许多重要的身体功能，因此应进行彻底研究，以了解其生物学作用及其与疾病的关系。从天然来源中分离大量均相状态的唾液酸聚糖的困难激发了相应的化学合成方法的发展，这些方法提供了可接受的纯度、产率和量。然而，由于唾液酸的α-糖基化的困难，相关的合成是具有挑战性的，这是由于其某些结构特征，例如在C3位置不存在立体定向基团和在异头位置存在羧基。此外，具有聚糖链上不同数量和位置的唾液酸的唾液酸聚糖的结构复杂性构成了额外的障碍。因此，尽管已经开发了各种类型的唾液酸供体/受体用于直接合成α-唾液酸糖苷，但仍然高度追求有效的α-立体选择性途径。在此，我们综述了唾液酸苷的α立体选择性合成及其在神经节苷脂和其他唾液酸聚糖制备中的应用的最新进展。
Sialic acid is an important component of cell surface glycans, which are responsible for many vital body functions and should therefore be thoroughly studied to understand their biological roles and association with disorders. The difficulty of isolating large quantities of homogenous‐state sialoglycans from natural sources has inspired the development of the corresponding chemical synthesis methods affording acceptable purities, yields, and amounts. However, the related syntheses are challenging because of the difficulties in α‐glycosylation of sialic acid, which arises from its certain structural features such as the absence of a stereodirecting group at the C3 position and presence of carboxyl group at the anomeric position. Moreover, the structural complexities of sialoglycans with diverse numbers and locations of sialic acid on the glycan chains pose additional barriers. Thus, efficient α‐stereoselective routes to sialosides remain highly sought after, although various types of sialyl donors/acceptors have been developed for the straightforward synthesis of α‐sialosides. Herein, we review the latest progress in the α‐stereoselective synthesis of sialosides and their applications in the preparation of gangliosides and other sialoglycans.