Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Prof. García González 1, Seville 41012, Spain.
Beilstein J Org Chem. 2010 Feb 22;6:20. doi: 10.3762/bjoc.6.20.
Oligosaccharides are currently recognised as having functions that influence the entire spectrum of cell activities. However, a distinct disadvantage of naturally occurring oligosaccharides is their metabolic instability in biological systems. Therefore, much effort has been spent in the past two decades on the development of feasible routes to carbohydrate mimetics which can compete with their O-glycosidic counterparts in cell surface adhesion, inhibit carbohydrate processing enzymes, and interfere in the biosynthesis of specific cell surface carbohydrates. Such oligosaccharide mimetics are potential therapeutic agents against HIV and other infections, against cancer, diabetes and other metabolic diseases. An efficient strategy to access this type of compounds is the replacement of the glycosidic linkage by amide or pseudoamide functions such as thiourea, urea and guanidine. In this review we summarise the advances over the last decade in the synthesis of oligosaccharide mimetics that possess amide and pseudoamide linkages, as well as studies focussing on their supramolecular and recognition properties.
寡糖目前被认为具有影响细胞活动全谱的功能。然而，天然存在的寡糖的一个明显缺点是它们在生物系统中的代谢不稳定性。因此，在过去的二十年中，人们花费了大量的精力来开发可行的途径，以获得碳水化合物类似物，这些类似物可以在细胞表面黏附中与 O-糖苷类似物竞争，抑制碳水化合物加工酶，并干扰特定细胞表面碳水化合物的生物合成。这些寡糖类似物是针对 HIV 和其他感染、癌症、糖尿病和其他代谢疾病的潜在治疗剂。获得这类化合物的一种有效策略是用酰胺或假酰胺官能团（如硫脲、脲和胍）取代糖苷键。在这篇综述中，我们总结了过去十年中在合成具有酰胺和假酰胺键的寡糖类似物方面的进展，以及专注于它们的超分子和识别特性的研究。
