Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
Molecules. 2023 Jun 12;28(12):4724. doi: 10.3390/molecules28124724.
Amino sugars are a kind of carbohydrates with one or more hydroxyl groups replaced by an amino group. They play crucial roles in a broad range of biological activities. Over the past few decades, there have been continuing efforts on the stereoselective glycosylation of amino sugars. However, the introduction of glycoside bearing basic nitrogen is challenging using conventional Lewis acid-promoted pathways owing to competitive coordination of the amine to the Lewis acid promoter. Additionally, diastereomeric mixtures of -glycoside are often produced if aminoglycoside lack a C2 substituent. This review focuses on the updated overview of the way to stereoselective synthesis of 1,2--aminoglycoside. The scope, mechanism, and the applications in the synthesis of complex glycoconjugates for the representative methodologies were also included.
氨基糖是一类含有一个或多个羟基被氨基取代的碳水化合物。它们在广泛的生物活性中起着至关重要的作用。在过去的几十年中，人们一直在努力实现氨基糖的立体选择性糖基化。然而，由于伯胺与路易斯酸催化剂的竞争性配位，使用传统的路易斯酸促进途径来引入带有碱性氮的糖苷是具有挑战性的。此外，如果氨基糖苷缺乏 C2 取代基，通常会产生 -糖苷的非对映异构体混合物。本文综述了 1,2--氨基糖苷立体选择性合成方法的最新进展。还包括了代表性方法在合成复杂糖缀合物中的范围、机制和应用。
