Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750

Abstract

Mandelic acid was produced from racemic mandelonitrile by Akcaligenes 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.

Autodisplay of Nitrilase from Alcaligenes faecalis in E. coli Yields a Whole Cell Biocatalyst for the Synthesis of Enantiomerically Pure (R)‐Mandelic Acid

“…The mobile phase consisted of hexane (90 %, v/v), isopropyl alcohol (10 %, v/v) and trifluoroacetic acid (0.1 %, v/v). The mandelic acid was extracted from the bioconversion samples as described elsewhere, with the slight modification in that ethyl acetate was used instead of dichloromethane 28…”

Efficient separation of (R)‐(‐)‐mandelic acid biosynthesized from (R,S)‐mandelonitrile by nitrilase using ion‐exchange process

“…Anionic form of R ‐MA was the predominant form in the bioreaction mixture because the biosynthesis of R ‐MA from racemic mandelonitrile with nitrilase was usually carried out under alkaline conditions 7, 8, 11–13, 17, 18. In this case, the anion ion‐exchange resin HZ202 has high affinity for R ‐MA 20.…”

“…Many studies on the biosynthesis of R ‐MA from racemic mandelinitrile with nitrilase have been published 6–17. Yamamoto et al 8, 10 investigated the production of R ‐MA from racemic mandelonitrile by Alcaligenes faecalis ATCC 8750. The reaction yield from the racemate reached 91%, and the enantiomeric excess ( ee ) of product was kept above 99%.…”

“…However, little research on the recovery of R ‐MA has been reported. The traditional method used for R ‐MA recovery from the bioreaction mixture is organic solvent extraction 8, 9, 11. This method is inefficient, has high solvent consumption and results in low recovery of product.…”

Hydrolysis of nitriles by soil bacteria: variation with soil origin

“…It is noteworthy that the Rhodococci were unusually poor at converting this substrate. M195 and M208 were similar to Bacillus cereus, which is a known nitrile converter (Saroja et al 2000), while M148 was closely clustered to Alcaligenes faecalis, which is also known to convert nitriles (Yamamoto et al 1991). Species of Bacillus and Alcaligenes have been isolated from cyanide containing mine tailings previously (Ingvorsen et al 1991;Meyers et al 1991Meyers et al , 1993.…”