Aminooxylated Carbohydrates: Synthesis and Applications,Chemical Reviews

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Aminooxylated Carbohydrates: Synthesis and Applications
Chemical Reviews ( IF 51.4 ) Pub Date : 2017-07-06 00:00:00 , DOI: 10.1021/acs.chemrev.6b00733
Carlo Pifferi ₁ , Gour Chand Daskhan ₁ , Michele Fiore ₁ , Tze Chieh Shiao ₂ , René Roy ₂ , Olivier Renaudet _{1,

3}

Affiliation

Among other classes of biomolecules, carbohydrates and glycoconjugates are widely involved in numerous biological functions. In addition to addressing the related synthetic challenges, glycochemists have invested intense efforts in providing access to structures that can be used to study, activate, or inhibit these biological processes. Over the past few decades, aminooxylated carbohydrates have been found to be key building blocks for achieving these goals. This review provides the first in-depth overview covering several aspects related to the syntheses and applications of aminooxylated carbohydrates. After a brief introduction to oxime bonds and their relative stabilities compared to related C═N functions, synthetic aspects of oxime ligation and methodologies for introducing the aminooxy functionality onto both glycofuranosyls and glycopyranosyls are described. The subsequent section focuses on biological applications involving aminooxylated carbohydrates as components for the construcion of diverse architectures. Mimetics of natural structures represent useful tools for better understanding the features that drive carbohydrate–receptor interaction, their biological output and they also represent interesting structures with improved stability and tunable properties. In the next section, multivalent structures such as glycoclusters and glycodendrimers obtained through oxime ligation are described in terms of synthetic design and their biological applications such as immunomodulators. The second-to-last section discusses miscellaneous applications of oxime-based glycoconjugates, such as enantioselective catalysis and glycosylated oligonucleotides, and conclusions and perspectives are provided in the last section.

中文翻译：

氨基氧化碳水化合物：合成与应用

在其他种类的生物分子中，碳水化合物和糖缀合物广泛参与许多生物学功能。除了解决相关的合成难题外，糖化学家还投入了巨大的努力来提供可用于研究，激活或抑制这些生物学过程的结构。在过去的几十年中，已发现氨基氧化的碳水化合物是实现这些目标的关键组成部分。这篇综述提供了第一个深入的概述，涵盖了与氨基氧化碳水化合物的合成和应用有关的几个方面。在简要介绍了肟键及其与相关C═N函数相比的相对稳定性之后，描述了肟连接的合成方面以及用于将氨基氧基官能团引入糖呋喃糖基和糖吡喃糖基的方法。接下来的部分集中在涉及氨基氧化的碳水化合物作为构建多种结构的组分的生物学应用中。天然结构的模拟物是有用的工具，可用于更好地理解驱动碳水化合物与受体相互作用的特征，其生物输出，并且它们还代表具有改进的稳定性和可调性的有趣结构。在下一部分中，将通过合成设计及其生物学应用（例如免疫调节剂）来描述通过肟连接获得的多价结构（例如糖簇和糖树状聚合物）。

更新日期：2017-07-06

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