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Chemoenzymatic microfluidic cascade reaction: Coupling of a diels-alder reaction with a transketolase-catalyzed reaction

Santos, M; O'Sullivan, B; Müller, S; Bunescu, A; Baganz, F; Marques, MPC; Hailes, H; ... Wohlgemuth, R; + view all (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. Green open access

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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.

Type: Proceedings paper
Title: Chemoenzymatic microfluidic cascade reaction: Coupling of a diels-alder reaction with a transketolase-catalyzed reaction
Event: MicroTAS 2020 - 24th International Conference on Miniaturized Systems for Chemistry and Life Sciences
Open access status: An open access version is available from UCL Discovery
Publisher version: https://cbmsociety.org/microtas/microtas_proceedin...
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: Chemoenzymatic reaction, Diels-Alder, Transketolase, Microfluidic cascade
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science > Dept of Biochemical Engineering
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10118974
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