An expedient enzymatic route to isomeric 2-, 3- and 6-monodeoxy-monofluoro-maltose derivatives

2-Deoxy-2-fluoro-d-glucose, 3-deoxy-3-fluoro-d-glucose and 6-deoxy-6-fluoro-d-glucose were converted into the corresponding maltose derivatives using Arabidopsis thaliana DPE2-mediated trans-glycosylation reaction with glycogen acting as a glucosyl donor. 19F NMR spectroscopy proved to be a valuable tool for monitoring the progress of these reactions and to assess the nature of resulting oligomeric products.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Three GH77 glycosidases were assessed for glucosylation of fluoroglucose with a glycogen donor. ► Deoxy-fluoro-maltose derivatives were synthesised using Arabidopsis trans-glycosidase DPE2. ► 19F NMR spectroscopy proved useful for following trans-glycosylation reactions of fluorosugars.