Thirteen glucose analogues bearing electrophilic groups were synthesized (five of themfor the first time) and screened as inhibitors of the glucose transporter (EII Glc )of the Escherichia coli phosphoenolpyruvate–sugar phospho-transferase system (PTS). 2¢,3¢-Epoxypropyl b-D-glucopyr-anoside (3a) is an inhibitor and also a pseudosubstrate. Five analogues are inhibitorsofnonvectorialGlcphosphorylation by EII Glc but not pseudosubstrates.