Aldol reactions play an important role in organic synthesis, as they belong to the class of highly beneficial C-C-linking reactions. Aldol type reactions can be efficiently and stereoselectively catalyzed by… Click to show full abstract
Aldol reactions play an important role in organic synthesis, as they belong to the class of highly beneficial C-C-linking reactions. Aldol type reactions can be efficiently and stereoselectively catalyzed by the enzyme 2-Deoxy-D-ribose-5-phosphate aldolase (DERA) to gain key intermediates for pharmaceuticals like atorvastatin. The immobilization of DERA would open the opportunity for a continuous operation mode which gives access to an efficient, large-scale production of respective organic intermediates. In this contribution, we synthesize and utilize DERA/polymer conjugates for the generation and fixation of a DERA bearing thin film on a polymeric membrane support. The conjugation strongly increases the tolerance of the enzyme towards the industrial relevant substrate acetaldehyde while UV-crosslinkable groups along the conjugated polymer chains provide the opportunity for covalent binding to the support. First, we provide a thorough characterization of the conjugates followed by immobilization tests on representative, non-porous cycloolefinic copolymer supports. Finally, immobilization on the target supports constituted of polyacrylonitrile (PAN) membranes is performed and the resulting enzymatically active membranes are implemented in a simple membrane module setup for a first assessment of biocatalytic performance in continuous operation mode using the combination hexanal/acetaldehyde as substrate.
               
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