Acyloin formation by benzoylformate decarboxylase from Pseudomonas putida.
Whole cells and cell extracts of Pseudomonas putida grown in a medium containing ammonium mandelate have the capacity to produce the acyloin compound 2-hydroxypropiophenone when incubated with benzoylformate and acetaldehyde. Benzaldehyde and benzyl alcohol were formed as reaction by-products. The enantiomeric excess of the 2-hydroxypropiophenone product was found to be 91 to 92%. The absolute configuration of the enzymatically prepared product at the carbinol carbon was found to be S. The thiamine PPi-linked enzyme benzoylformate decarboxylase, purified to give a single protein band on polyacrylamide gel electrophoresis, was shown to be responsible for the catalysis of this novel condensation reaction.
Wilcocks
R
R
Department of Biology, University of Waterloo, Ontario, Canada.
Ward
O P
OP
Collins
S
S
Dewdney
N J
NJ
Hong
Y
Y
Prosen
E
E
D001547:Benzaldehydes / Q000378:metabolism; D001711:Biotransformation; D002262:Carboxy-Lyases / Q000378:metabolism*; D005233:Fatty Alcohols / Q000378:metabolism*; D006910:Hydroxypropiophenone / Q000378:metabolism; D016958:Pseudomonas putida / Q000201:enzymology / Q000378:metabolism*
D001547:Benzaldehydes; D005233:Fatty Alcohols; D006910:Hydroxypropiophenone; C011159:acyloin; D002262:Carboxy-Lyases; C019778:benzoylformate decarboxylase; C032175:benzaldehyde