Enzymatic Transformations 63. High-Concentration Two Liquid-Liquid PhaseAspergillus niger Epoxide Hydrolase-Catalysed Resolution: Application to Trifluoromethyl-Substituted Aromatic Epoxides

Autor: Alain Archelas, Jean-Marc Paris, Fabien Barbirato, Justine Deregnaucourt, Roland Furstoss
Rok vydání: 2007
Předmět:
Zdroj: Advanced Synthesis & Catalysis. 349:1405-1417
ISSN: 1615-4169
1615-4150
Popis: The aim of this work was to perform dif- ferent studies allowing us to improve the methodolo- gy we had previously described to realise the Asper- gillus niger epoxide hydrolase-catalysed resolution of eight trifluoromethyl-substituted styrene oxide deriv- atives. A two liquid-liquid phase methodology was developed, for the first time with such an enzyme, using iso-octane as a co-solvent. Different experi- mental parameters like the global volume substrate concentration, the substrate over enzyme ratio, the agitation rate and the purity of the enzyme were also optimised. This allowed us to set up very efficient bi- oreactors allowing performance of the hydrolytic ki- netic resolution of the different substrates by operat- ing at room temperature (278C), within a few hours only and at a very high global volume substrate con- centration, i.e., 360 g/ L (1.8 M). The efficiencies of the Aspergillus niger epoxide hydrolase toward the different epoxides studied were compared and the productivity of the practical process was evaluated. These results amply demonstrated that, without con- test, the biocatalysed hydrolytic kinetic resolution of epoxides is nowadays to be considered as a very effi- cient, mild, cheap and easy-to-use "green chemistry" methodology applicable for cost effective preparative (i.e., industrial) scale implementation.
Databáze: OpenAIRE
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