Product selection in the dynamic enzymatic synthesis of cyclodextrins can be controlled by changing the pH. Using cyclodextrin glucanotransferase to make labile the glycosidic linkages in cyclodextrins (CDs), a dynamic combinatorial library of interconverting linear and cyclic α-1,4-glucans was generated. Templates can be employed to favour the selective production of specific CDs and, herein, we show that by using ionisable templates, the synthesis of α-CD or β-CD can be favoured by simply changing the pH. Using 4-nitrophenol as the template, β-CD is the preferred product at low pH, while α-CD is the preferred product at high pH. Furthermore, a new methodology is described for the simulation of product distributions in dynamic combinatorial libraries with ionisable templates at any given pH.
Lisa Samuelsen, Dennis Larsen, Christian Schönbeck and Sophie R. Beeren (2022) pH-Responsive templates modulate the dynamic enzymatic synthesis of cyclodextrins. Chem. Commun., 58, 5152-5155. https://doi.org/10.1039/D1CC06554H