Synthesis of a series of maltotriose phosphates with an evaluation of the utility of a fluorous phosphate protecting group

A series of methyl maltotrioside phosphates were synthesized for application in the determination of the actual molecular substrate of the Lafora enzyme involved in Lafora disease. Several different synthetic routes were applied for the successful synthesis of six methyl maltotrioside phosphate regioisomers. The utility of a new fluorous phosphate protecting group was also evaluated, but its utility was found to be limited in this particular late stage introduction.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Six methyl maltotrioside phosphates were synthesized. ► Three different routes starting from methyl glucoside and maltose were used in the synthesis. ► The utility of a new fluorous phosphate protecting group was evaluated in the context of this synthesis. ► The final phosphate isomers are designed to identify the substrate of a key enzyme involved in Lafora disease.