This account describes our efforts dedicated to: 1) the design of glycomimetics aimed at targeting therapeutically relevant carbohydrate processing enzymes, and 2) the observation, characterization, and exploitation of glycosyl cations as a tool for studying the glycosylation reaction. These findings have brought important data regarding this key ionic species as well as innovative strategies to access iminosugars of interest.

1 Introduction

2 The Glycosyl Cation, A Central Species in Glycosciences

2.1 A Selection of the Strategies Developed so far to Gain Insights into Glycosyl Cations Structure

2.2 When Superacids Meet Carbohydrates

3 Chemical Probes to Gain Insights into the Pseudorotational Itinerary of Glycosides During Glycosidic Bond Hydrolysis

3.1 Conformationally Locked Glycosides

3.1.1 The Xylopyranose Case

3.1.2 The Mannopyranose Case

3.2 Conformationally Flexible Iminosugars

3.2.1 Nojirimycin Ring Homologues

3.2.2 Noeuromycin Ring Homologues

3.2.3 Seven-Membered Iminosugar C-Glycosides

4 N-Acetyl-d-glucosamine Mimics

5 Ring Contraction: A Useful Tool to Increase Iminosugar’s Structural Diversity

6 Regioselective Deprotection of Iminosugar C-Glycosides to Introduce Diversity at C2 Position

7 Conclusion

该文献描述了我们致力于以下方面的努力：1）设计针对药物的相关糖类加工酶的糖模拟物，以及2）糖基阳离子的观察，表征和开发，作为研究糖基化反应的工具。这些发现带来了有关该关键离子物种的重要数据，以及获取感兴趣的亚氨基糖的创新策略。

1引言

2糖基阳离子，糖科学的中心物种

2.1迄今为止为了解糖基阳离子结构而制定的策略

2.2当超强酸遇到碳水化合物时

3种化学探针，可帮助您深入了解糖苷键水解过程中糖苷的假旋转行程

3.1构型锁定的糖苷

3.1.1木吡喃糖情况

3.1.2甘露吡喃糖情况

3.2构形灵活的氨基糖

3.2.1诺奇霉素环同源物

3.2.2新霉素环同源物

3.2.3七糖氨基糖C-糖苷

4 N-乙酰基-d-葡萄糖胺模拟物

5环收缩：增加氨基糖结构多样性的有用工具

6氨基糖C-糖苷的区域选择性脱保护以在C2位置引入多样性

7结论