Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.
Org Lett. 2021 Dec 17;23(24):9516-9519. doi: 10.1021/acs.orglett.1c03723. Epub 2021 Nov 30.
Cyclophellitols are potent inhibitors of exo- and endoglycosidases. Efficient synthetic methodologies are needed to fully capitalize on this intriguing class of mechanism-based enzyme deactivators. We report the synthesis of an orthogonally protected cyclitol from d-glucal (19% yield over 12 steps) and its use in the synthesis of α-(1,3)-linked di- and trisaccharide dextran mimetics. These new glycomimetics may find use as Dextranase inhibitors, and the developed chemistries in widening the palette of glycoprocessing enzyme-targeting glycomimetics.
环磷醇是外切糖苷酶和内切糖苷酶的有效抑制剂。需要有效的合成方法来充分利用这一类基于机制的酶失活剂。我们报告了从 D-葡萄糖醛(12 步总收率 19%)合成正交保护环糖醇的方法,并将其用于合成α-(1,3)-连接的二糖和三糖葡聚糖类似物。这些新的糖类似物可能作为葡聚糖酶抑制剂使用,并且所开发的化学方法拓宽了糖基化酶靶向糖类似物的范围。