Transaminase-membrane reactor for intensified chiral amines synthesis
(2023) Europacat2023 - 15th European Congress on Catalysis — Location: Praha, Czech Republic (2023.August.27AD)
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- Introduction. Chiral amines are essential building blocks for the pharmaceutical industry. Their synthesis often involves multi-step processes requiring costly organometallic homogeneous catalysts [1]. Amine transaminases (ATAs) may provide greener routes to produce chiral amines with excellent enantioselectivity. Yet, industrial applications of ATAs remain restricted to batch processes in which ATAs are employed as free enzymes (non-reusable). One can thus design more versatile heterogeneous biocatalysts able to operate in flow, by immobilizing ATAs on solid supports [2]. Importantly, most targeted transaminations are limited by unfavourable thermodynamics. One strategy to shift the equilibrium towards high chiral amine yields, is the set-up of combined reaction-purification processes. Hence, coupling transaminases with membrane technology in an enzyme membrane reactor is of particular interest, as it could allow the removal of products during operation. Experimental/methodology. As a proof of concept, we present the immobilization of an ATA from Halomonas elongata (HeWT) onto polypropylene (PP) and polyacrylonitrile (PAN) membranes and its application to catalyze the enantioselective synthesis of a model chiral amine in batch (Fig. 1). Briefly, PAN surface was chemically modified and coated with polyethyleneimine (PEI) to attract HeWT via electrostatic interactions. Glutaraldehyde (GA) was then used to cross-link the loosely attached HeWT and prevent their leaching from the membrane surface. On PP membranes, a covalent grafting strategy was adopted. PP surface was coated with polydopamine (PD) which provided amine functions for further functionalization. The subsequent addition of glycerol diglycidyl ether (GDE) enabled a strong grafting of the enzyme, especially when it was partially derivatized with PEI prior to immobilization. Results and discussion. The obtained heterogenized ATAs are robust and recyclable, as they successfully performed successive catalytic cycles without deactivation, and with negligeable leaching (as confirmed by hot filtration test). They also showed good (30 %) activity recovery and enhanced stability compared to their soluble counterparts. Thus, we demonstrate the use of novel immobilized ATA carrier materials well-suited for upcoming flow operations, paving the way to intensified processes for chiral amines production.
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Meersseman Arango, H., Leyssens, T., Luis Alconero, P., Paradisi, F., & Debecker, D. (2023). Transaminase-membrane reactor for intensified chiral amines synthesis. Europacat2023 - 15th European Congress on Catalysis, Praha, Czech Republic. https://hdl.handle.net/2078.5/25461