Chemoenzymatic synthesis in flow reactors: a rapid and convenient preparation of captopril
- Dr. Valerio De Vitis1
- Dr. Federica Dall'Oglio1
- Dr. Andrea Pinto2
- Prof. Carlo De Micheli2
- Prof. Francesco Molinari1
- Prof. Paola Conti2
- Dr. Diego Romano1
- Dr. Lucia Tamborini2
- 1 Department of Food Environmental and Nutritional Science, University of Milan, Milan, Italy
- 2 Department of Pharmaceutical Sciences, University of Milan, Milan, ItalyRead the publication that featured this abstract
The chemoenzymatic flow synthesis of enantiomerically pure captopril, a widely used antihypertensive drug, is accomplished starting from simple, inexpensive, and readily available reagents. The first step is a heterogeneous biocatalyzed regio- and stereoselective oxidation of cheap prochiral 2-methyl-1,3-propandiol, performed in flow using immobilized whole cells of Acetobacter aceti MIM 2000/28, thus avoiding the use of aggressive and environmentally harmful chemical oxidants. The isolation of the highly hydrophilic intermediate (R)-3-hydroxy-2-methylpropanoic acid is achieved in-line by using a catch-and-release strategy. Then, three sequential high-throughput chemical steps lead to the isolation of captopril in only 75 min. In-line quenching and liquid–liquid separation enable breaks in the workflow and other manipulations to be avoided.
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