立体选择性唾液酸化的先进化学方法及其在唾液酸合成中的应用,The Chemical Record

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立体选择性唾液酸化的先进化学方法及其在唾液酸合成中的应用
The Chemical Record ( IF 7.0 ) Pub Date : 2021-05-24 , DOI: 10.1002/tcr.202100080
Amol M Vibhute ₁ , Naoko Komura ₁ , Hide-Nori Tanaka ₁ , Akihiro Imamura _{1,

2} , Hiromune Ando ₁

Affiliation

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，因此应彻底研究以了解它们的生物学作用和与疾病的关联。从天然来源中分离大量同质唾液酸聚糖的困难激发了相应化学合成方法的发展，以提供可接受的纯度、产率和数量。然而，由于唾液酸的α-糖基化困难，相关合成具有挑战性，这是由其某些结构特征引起的，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。而且，唾液酸在聚糖链上具有不同数量和位置的唾液酸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-唾液酸苷，但对唾液酸苷的有效 α-立体选择性途径仍然受到高度追捧。在此，我们回顾了唾液酸苷的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。

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Advanced Chemical Methods for Stereoselective Sialylation and Their Applications in Sialoglycan Syntheses

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.

更新日期：2021-05-24

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