School of Chemistry, University of Southampton, Highfield, Southampton SO171BJ, UK.
Org Biomol Chem. 2019 May 29;17(21):5331-5340. doi: 10.1039/c9ob00707e.
Fluorinated carbohydrates have been employed as probes for fundamental studies of protein-carbohydrate interactions, but also in the development of mechanism-based enzyme inhibitors. There is a continuing demand for novel fluorinated carbohydrate probes. Whereas most examples so far involved monodeoxyfluorinated sugars, multiply deoxyfluorinated sugars have gained much interest. Here we report the synthesis and characterisation of novel vicinal dideoxy-difluorinated d-galactoses with fluorination at the 3,4-positions, and at the 2,3-positions, the latter in both the pyranose and furanose forms. This includes a successful pyranose-into-furanose isomerisation protocol.
氟化碳水化合物已被用作研究蛋白质-碳水化合物相互作用的基本探针，也被用于开发基于机制的酶抑制剂。目前，人们对新型氟化碳水化合物探针的需求持续增长。到目前为止，大多数例子都涉及单脱氧氟化糖，而多脱氧氟化糖则引起了广泛关注。在这里，我们报告了新型 3,4-位和 2,3-位双脱氧-二氟化 D-半乳糖的合成和表征，后者在吡喃糖和呋喃糖形式中均有存在，包括成功的吡喃糖到呋喃糖的异构化方案。
