Biotransformation of benzaldehyde into (R)-phenylacetylcarbinol by filamentous fungi or their extracts.
Extracts of 14 filamentous fungi were examined regarding their potential for production of (R)-phenylacetylcarbinol [(R)-PAC], which is the chiral precursor in the manufacture of the pharmaceuticals ephedrine and pseudoephedrine. Benzaldehyde and pyruvate were transformed at a scale of 1.2 ml into PAC by cell-free extracts of all selected strains, covering the broad taxonomic spectrum of Ascomycota, Zygomycota and Basidiomycota. Highest final PAC concentrations were obtained with the extracts of Rhizopus javanicus and Fusarium sp. [78-84 mM (11.7-12.6 g/l) PAC within 20 h from initial substrate concentrations of 100 mM benzaldehyde and 150 mM pyruvate]. (R)-PAC was in about 90-93% enantiomeric excess. Rhizopus javanicus had the advantage of faster growth than Fusarium sp. Rhizopus javanicus mycelia were used as an example in a biotransformation process based on whole cells and benzaldehyde and glucose as substrates. The substrate pyruvate was generated through the fungal fermentation of glucose. Only 19 mM PAC (2.9 g/l) were produced within 8 h from 80 mM benzaldehyde. with evidence of significant benzyl alcohol production.
Rosche
B
B
Department of Biotechnology, University of New South Wales, Sydney, Australia. B.Rosche@unsw.edu.au
Sandford
V
V
Breuer
M
M
Hauer
B
B
Rogers
P
P
D000096:Acetone / Q000031:analogs & derivatives* / Q000378:metabolism / Q000493:pharmacokinetics*; D001547:Benzaldehydes / Q000378:metabolism / Q000493:pharmacokinetics*; D018533:Biomass; D001711:Biotransformation; D005658:Fungi / Q000378:metabolism*; D019289:Pyruvic Acid / Q000378:metabolism
D001547:Benzaldehydes; D000096:Acetone; D019289:Pyruvic Acid; C035293:1-hydroxy-1-phenyl-2-propanone; C032175:benzaldehyde