“Locked-ring” C-glycoside derivatives may be prepared wherein the ring of the sugar molecule remains intact without the need for any protecting groups. These C-glycoside derivatives may be produced by first reacting an aldose reducing sugar, which may be a hexose or a pentose, with a β-diketone to form a C-glycoside ketone. The C-glycoside ketone is then reacted with a ketone reactive compound, such as a hydrazine or hydroxylamine, optionally linked to a detectable label, to form a C-glycoside derivative wherein the ketone reactive compound is conjugated to the C-glycoside at the site of the ketone. The aldose reducing sugar used in the first reaction may a simple pentose or hexose monosaccharide, or it may be optionally substituted.
可以制备“锁定环”C-糖苷衍
生物,其中糖分子的环保持完整,无需任何保护基团。这些C-糖苷衍
生物可以通过首先将醛糖还原糖(可以是己糖或戊糖)与
β-二酮反应以形成C-糖苷酮。然后,将C-糖苷酮与酮反应性化合物(如
肼或
羟胺,可选地连接到可检测的标记)反应,形成一个C-糖苷衍
生物,其中酮反应性化合物与C-糖苷在酮的位置结合。在第一反应中使用的醛糖还原糖可以是简单的戊糖或己糖
单糖,也可以是可选择地取代的。