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Reaction engineering of biocatalytic (S)-naproxen synthesis integrating in-line process monitoring by Raman spectroscopy

Abstract

Biocatalytic (S)-naproxen synthesis by a (S)-selective arylmalonate decarboxylase mutant (AMDase G74C/M159L/C188G/V43I/A125P/V156L, AMDase-CLGIPL) exposes a promising environmentally friendly alternative to conventional chemical synthesis strategies. The reaction progress of naproxen synthesis catalyzed by covalently immobilized AMDase-CLGIPL onto a robust acrylate carrier was investigated with respect to reaction engineering. Kinetic characterization of the immobilized enzyme reveals a KM value of 22.1 ± 0.1 mM in the naproxen malonate conversion and an inhibiting effect of the produced naproxen with a Ki of 26.3 ± 1.4 mM. However, an effective process can be realized without in situ product removal yielding (S)-naproxen with an ee of 99%. By optimizing the product work up, an isolated yield of 92% was achieved with total turnover numbers between 83,000 and 107,000 in five repetitive batches. Furthermore, process monitoring with in-line Raman spectroscopy was successfully applied to analyze reaction progress with a root mean square error of prediction of 0.8 mM (corresponding to 4%).

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Publication details

The article was received on 01 Apr 2017, accepted on 19 May 2017 and first published on 19 May 2017


Article type: Paper
DOI: 10.1039/C7RE00043J
Citation: React. Chem. Eng., 2017, Accepted Manuscript
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    Reaction engineering of biocatalytic (S)-naproxen synthesis integrating in-line process monitoring by Raman spectroscopy

    M. Aßmann, A. Stöbener, C. Mügge, S. K. Gaßmeyer, L. Hilterhaus, R. Kourist, A. Liese and S. Kara, React. Chem. Eng., 2017, Accepted Manuscript , DOI: 10.1039/C7RE00043J

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