Institut Européen de Chimie et Biologie, Université de Bordeaux, 2 rue Robert Escarpit, 33607, Pessac, France.
Institut de Neurosciences Cognitives et Intégratives d'Aquitaine, CNRS UMR5287, Bordeaux, France.
Angew Chem Int Ed Engl. 2019 Mar 22;58(13):4281-4285. doi: 10.1002/anie.201814266. Epub 2019 Feb 19.
The metabolic oligosaccharide engineering (MOE) strategy using unnatural sialic acids has recently enabled the visualization of the sialome in living systems. However, MOE only reports on global sialylation and dissected information regarding subsets of sialosides is missing. Described here is the synthesis and utilization of sialic acids modified with a sydnone reporter for the metabolic labeling of sialoconjugates. The positioning of the reporter on the sugar significantly altered its metabolic fate. Further in vitro enzymatic assays revealed that the 9-modified neuraminic acid is preferentially accepted by the sialyltransferase ST6Gal-I over ST3Gal-IV, leading to the favored incorporation of the reporter into linkage-specific α2,6-N-linked sialoproteins. This sydnone sugar presents the possibility of investigating the roles of specific sialosides.
代谢寡糖工程（MOE）策略使用非天然唾液酸最近使唾液组在活系统中的可视化成为可能。然而，MOE 仅报告了全局唾液酸化，并且缺少有关唾液苷亚类的细分信息。本文描述了带有 sydnone 报告基团修饰的唾液酸的合成和利用，用于唾液酸缀合物的代谢标记。报告基团在糖上的定位显着改变了其代谢命运。进一步的体外酶测定表明，9-修饰的神经氨酸被唾液酸转移酶 ST6Gal-I 优先接受，而不是 ST3Gal-IV，从而有利于将报告基团掺入到具有特定连接的 α2,6-N-连接的唾液蛋白中。这种 sydnone 糖为研究特定唾液苷的作用提供了可能性。
