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Issue 4, 2017
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Reaction engineering of biocatalytic (S)-naproxen synthesis integrating in-line process monitoring by Raman spectroscopy

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Abstract

Biocatalytic (S)-naproxen synthesis using an (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 AMDase-CLGIPL covalently immobilized 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 the reaction progress with a root mean square error of prediction of 0.8 mM (corresponding to 4%).

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

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Supplementary files

Article information


Submitted
01 Apr 2017
Accepted
19 May 2017
First published
19 May 2017

React. Chem. Eng., 2017,2, 531-540
Article type
Paper

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, 2, 531
DOI: 10.1039/C7RE00043J

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