An orthogonally protected cyclitol for the construction of nigerose- and dextran-mimetic cyclophellitols

Ofman, T.P.; Küllmer, F.; Marel, G.A. van der; Codée, J.D.C.; Overkleeft, H.S. (2021)

Article / Letter to editor

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.

• All authors: Ofman, T.P.; Küllmer, F.; Marel, G.A. van der; Codée, J.D.C.; Overkleeft, H.S.
• Date: 2021-11-30
• Journal: Organic Letters
• Volume: 23
• Issue: 24
• Pages: 9516 - 9519
• DOI: doi:10.1021/acs.orglett.1c03723
• Link: https://pubs.acs.org/doi/10.1021/acs.orglett.1c03723
• Grant number: ERC-CoG-726072 “GLYCONTROL”; ERC-2020-SyG-951231 “CARBOCENTRE”