Xavier Nuno M, Rauter Amélia P
Departmento de Química e Bioquímica/Centro de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Edificio C8, Campo Grande, Lisboa, Portugal.
Carbohydr Res. 2008 Jul 21;343(10-11):1523-39. doi: 10.1016/j.carres.2008.04.033. Epub 2008 May 3.
The alpha,beta-unsaturated carbonyl function occurs in a wide variety of bioactive natural products. It is usually associated with the bioactivities of these compounds and acts as Michael acceptors for the addition of protein nucleophilic groups. The design and synthesis of sugars containing this functionality has provided a wide range of compounds, which can serve as building blocks of high synthetic versatility. This review deals with the chemistry of sugar-based molecules bearing singly linked or fused unsaturated lactones and ketones along with that of pyranoid enones and enonolactones. Examples are given of their syntheses and transformations into a variety of complex sugar derivatives such as branched-chain sugars, C-nucleosides, C-glycosyl derivatives, and various natural products, including selected analogues.
α,β-不饱和羰基官能团存在于多种具有生物活性的天然产物中。它通常与这些化合物的生物活性相关联，并作为迈克尔受体用于蛋白质亲核基团的加成。含有这种官能团的糖类的设计与合成已产生了各种各样的化合物，这些化合物可作为具有高度合成通用性的构建单元。本综述涉及带有单键连接或稠合的不饱和内酯和酮的糖基分子的化学，以及吡喃型烯酮和烯醇内酯的化学。文中给出了它们的合成实例以及将它们转化为各种复杂糖衍生物的实例，这些衍生物包括支链糖、C-核苷、C-糖基衍生物以及各种天然产物，包括选定的类似物。
