Overcoming Water Insolubility in Flow: Enantioselective Hydrolysis of Naproxen Ester
- David Roura Padrosa1
- Valerio De Vitis2
- Martina Letizia Contente1*
- Francesco Molinari2
- Francesca Paradisi1*
- 1 School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK
- 2 Department of Food, Environmental and Nutritional Sciences (DeFENS), Università degli studi di Milano, Via Mongiagalli 25, 20133 Milan, Italy;
Read the publication that featured this abstractHydrolytic enantioselective cleavage of different racemic non-steroidal anti-inflammatory drugs (NSAIDs) ester derivatives has been studied. An engineered esterase form Bacillus subtilis (BS2m) significantly outperformed homologous enzymes from Halomonas elongata (HeE) and Bacillus coagulants (BCE) in the enantioselective hydrolysis of naproxen esters. Structural analysis of the three active sites highlighted key differences which explained the substrate preference. Immobilization of a chimeric BS2m-T4 lysozyme fusion (BS2mT4L1) was improved by resin screening achieving twice the recovered activity (22.1 ± 5 U/g) with respect to what had been previously reported, and was utilized in a packed bed reactor. Continuous hydrolysis of α-methyl benzene acetic acid butyl ester as a model substrate was easily achieved, albeit at low concentration (1 mM). However, the high degree of insolubility of the naproxen butyl ester resulted in a slurry which could not be efficiently bioconverted, despite the addition of co-solvents and lower substrate concentration (1 mM). Addition of Triton® X-100 to the substrate mix yielded 24% molar conversion and 80% e.e. at a 5 mM scale with 5 min residence time and sufficient retention of catalytic efficiency after 6 h of use.
Get in touch
For more information on flow chemistry systems and services please use the contact methods below.
Call us on +44 (0)1284 728659 or Email us
Resource Centre
R-Series

The Vapourtec R-Series is, quite simply, unrivalled for flow chemistry
- Flexible |
- Precise |
- Automatable
The R-Series is undoubtedly the most versatile, modular flow chemistry system available today.
E-Series

The Vapourtec E-Series is the perfect introductory system for flow chemistry
- Robust |
- Easy to use |
- Affordable
The E-Series is a robust and affordable, entry level flow chemistry system designed for reliability and ease of use.