Single enzyme coupled UDP-mediated transglycosylation reaction of 4-methylumbelliferone 54 with 2-chloro-4-nitrophenyl glucosamino/xylosaminosides. A) General reaction scheme. B) Time course of 5 fluorescence as a measure of reaction progress over 8 h with different UDP concentrations. C) HPLC chromatogram of the final reaction mixtures from panel c after 8 h where the solid circle (●) denotes the 54 glycoside product and (○) represents UDP-2-deoxy-2-amino-α-D-glucose. D) Percentage conversion to 54 glycoside products via OleD Loki-catalyzed NDP-mediated transglycosylation containing 0.1 mM UDP, 1 mM 54, and 1 mM 2-chloro-4-nitrophenyl glycoside donors (1, 2, 3, 5, 7, 9, 13) (n ≥ 2. S. D. < 5%).