Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750.
R-(-)-Mandelic acid was produced from racemic mandelonitrile by Alcaligenes faecalis ATCC 8750. Ammonium acetate or L-glutamic acid as the carbon source and n-butyronitrile as the inducer in the culture medium were effective for bacterial growth and the induction of R-(-)-mandelic acid-producing activity. The R-(-)-mandelic acid formed from mandelonitrile by resting cells was present in a 100% enantiomeric excess. A. faecalis ATCC 8750 has an R-enantioselective nitrilase for mandelonitrile and an amidase for mandelamide. As R-(-)-mandelic acid was produced from racemic mandelonitrile in a yield of 91%, whereas no S-mandelonitrile was left, the S-mandelonitrile remaining in the reaction is spontaneously racemized because of the chemical equilibrium and is used as the substrate. Consequently, almost all the mandelonitrile is consumed and converted to R-(-)-mandelic acid. R-(-)-Mandelic acid was also produced when benzaldehyde plus HCN was used as the substrate.
Yamamoto
K
K
Pharmaceutical Research and Development Department, Asahi Chemical Industry Company Ltd., Miyazaki, Japan.
Oishi
K
K
Fujimatsu
I
I
Komatsu
K
K
D000097:Acetonitriles / Q000378:metabolism*; D000421:Alcaligenes / Q000201:enzymology / Q000254:growth & development* / Q000378:metabolism; D000581:Amidohydrolases / Q000378:metabolism; D001547:Benzaldehydes / Q000378:metabolism; D002244:Carbon / Q000494:pharmacology; D006856:Hydrogen Cyanide / Q000378:metabolism; D006868:Hydrolysis; D007536:Isomerism; D007700:Kinetics; D008333:Mandelic Acids / Q000378:metabolism*; D013379:Substrate Specificity
D000097:Acetonitriles; D001547:Benzaldehydes; D008333:Mandelic Acids; D006856:Hydrogen Cyanide; C045516:mandelonitrile; D002244:Carbon; D000581:Amidohydrolases; C037938:mandelic acid; C032175:benzaldehyde