A series of 3-deoxy-3-N-arylated-β-d-galactoside and -guloside derivatives have been synthesized by cesium fluoride/trimetylsilylaryl triflate-mediated benzyne generation and N-arylation of 3-deoxy-3-amino-β-d-galactosides and -gulosides, respectively. Evaluation as ligands to galectin-1, 2, 3, 4N (N-terminal domain), 4C (C-terminal domain), 7, 8N, 8C, 9C, and 9N revealed that the galactosides selectively bound galectin-9C, whereas the gulosides selectively bound galectin-9N. Hence, the N-aryl group induces galectin-9 selectivity and the ligand 3C-configuration acts as an epimeric selectivity switch between the two domains of galectin-9. Furthermore, MD simulations revealed that galacto derivatives in galectin-9C and gulo derivatives in galectin-9N find stable poses with specific interactions, which proposes a possible explanation to the gal/gulo 9C/9N selectivity.

中文翻译：

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Epimers切换Galectin-9域选择性：3N-芳基半乳糖苷与C末端结合，而Gulosides与N末端结合。

通过氟化铯/三甲硅烷基甲硅烷基芳基三氟甲磺酸酯介导的苯炔生成和3-脱氧-3-氨基-β-的N-芳基化反应，合成了一系列3-脱氧-3-N-芳基-β-d-半乳糖苷和-古洛糖苷衍生物。分别为d-半乳糖苷和-gulosides。评估半乳糖凝集素-1、2、3、4N（N末端域），4C（C末端域），7、8N，8C，9C和9N的配体表明，半乳糖苷选择性结合半乳糖凝集素-9C，而半乳糖苷选择性结合半乳糖凝集素-9C。古洛糖苷选择性结合半乳糖凝集素9N。因此，N-芳基基团诱导半乳凝素9选择性，并且配体3C-构型充当半乳凝素9的两个结构域之间的差向异构体选择性开关。此外，MD模拟显示，galectin-9C中的半乳糖衍生物和galectin-9N中的gulo衍生物找到具有特定相互作用的稳定姿势，