Santos, M; O'Sullivan, B; Müller, S; Bunescu, A; Baganz, F; Marques, MPC; Hailes, H; ... Wohlgemuth, R; + view all Santos, M; O'Sullivan, B; Müller, S; Bunescu, A; Baganz, F; Marques, MPC; Hailes, H; Szita, N; Wohlgemuth, R; - view fewer (2020) Chemoenzymatic microfluidic cascade reaction: Coupling of a diels-alder reaction with a transketolase-catalyzed reaction. In: MicroTAS 2020 - 24th International Conference on Miniaturized Systems for Chemistry and Life Sciences. (pp. pp. 693-694). CBMS: Online conference.

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Abstract

A chemoenzymatic microfluidic cascade reaction is demonstrated for the first time, where a Diels-Alder reaction is followed by a transketolase reaction, for the synthesis of 3,4-dimethylcyclohex-3-ene-2’-keto-1’,3’- propanediols, which are used as scaffolds for a number of interesting pharmaceutical compounds. For an efficient organic synthesis, an enzymatic reaction would be advantageous, as it would minimize the number of process steps by eliminating the need for protective chemistry [1]. However, most catalysts and reactions conditions used with DA reactions are not compatible with a subsequent enzymatic reaction (issues revolve e.g. around solvent compatibility, differing reaction rates, and mis-match of pH). We used the spatial confinement of reactions afforded by cascaded microreactors, which has been well established for enzyme-enzyme reactions [2], to overcome these challenges and to achieve a chemoenzymatic reaction in continuous flow. Each reaction was optimized individually or in a step-wise synthesis, considering solvents and catalyst combinations, before being coupled in continuous flow.

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