The alkyne tag, consisting of only two carbons, is widely used as a bioorthogonal functional group due to its compactness and nonpolar structure, and various probes consisting of lipids bearing an alkyne tag have been developed. Here, we designed and synthesized analogues of ganglioside GM3 bearing an alkyne tag in the fatty acid moiety and evaluated the effect of the alkyne tag on the biological activity. To eliminate the influence of other factors such as degradation of the glycan chain when evaluating biological activity in a cellular environment, we introduced the tag into sialidase-resistant (S)-CHF-linked GM3 analogues developed by our group. The designed analogues were efficiently synthesized by tuning the protecting group of the glucosylsphingosine acceptor. The growth-promoting effect of these analogues on Had-1 cells was dramatically altered depending upon the position of the alkyne tag.

仅由两个碳组成的炔烃标签由于其紧凑性和非极性结构而被广泛用作生物正交官能团，并且已经开发了由带有炔烃标签的脂质组成的各种探针。在这里，我们设计并合成了在脂肪酸部分带有炔烃标签的神经节苷脂 GM3 类似物，并评估了炔烃标签对生物活性的影响。为了在细胞环境中评估生物活性时消除聚糖链降解等其他因素的影响，我们将标签引入抗唾液酸酶（S)-CHF-连接的 GM3 类似物由我们小组开发。通过调整葡萄糖基鞘氨醇受体的保护基团，可以有效地合成设计的类似物。这些类似物对 Had-1 细胞的生长促进作用会根据炔烃标签的位置发生显着变化。