Kitasato University, Tokyo, Japan.
Proc Jpn Acad Ser B Phys Biol Sci. 2011;87(6):328-61. doi: 10.2183/pjab.87.328.
Sialic acids are electronegatively charged C9-sugars and are considered to play important roles in higher animals and some microorganisms. Denoting their significance, understanding and exploiting the complexity of the sialic acids has been referred to as the "the third language of life". In essence, "sialic acid derivatives possess a harmonious shape and good balance between two opposing hydrophilic and hydrophobic parts, meaning that they should display various kinds of potentially unique and possibly conflicting physiological activities (glycolipoids)". Consequently, there are good omens that unprecedented 'miracle' medicines could be developed from sialic acid derivatives. In this review, the first problem, the preparation of sialic acids, is covered, the synthesis of sialic acid derivatives and confirmation of their structures obviously being of critical significance. In addition we needed to confirm their precise stereochemistry and a hydrolysis method has been developed for confirmation of the anomeric position. Several of the compounds have already demonstrated interesting bioactivity.
唾液酸是带负电荷的 C9 糖,被认为在高等动物和一些微生物中发挥着重要作用。鉴于其重要性,了解和利用唾液酸的复杂性被称为“生命的第三种语言”。从本质上讲,“唾液酸衍生物具有和谐的形状和良好的亲水和亲脂两部分之间的平衡,这意味着它们应该表现出各种潜在的独特的、可能相互冲突的生理活性(糖脂)”。因此,有很好的迹象表明,前所未有的“奇迹”药物可以从唾液酸衍生物中开发出来。在这篇综述中,首先讨论了唾液酸的制备问题,因为唾液酸衍生物的合成及其结构的确认显然具有至关重要的意义。此外,我们还需要确认其精确的立体化学,为此开发了一种水解方法来确认端基碳原子的构型。其中一些化合物已经表现出有趣的生物活性。