Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates.
Bacteria were enriched from soil samples with succinate as a carbon source and racemic naproxen nitrile [2-(6-methoxy-2-naphthyl)propionitrile] as sole source of nitrogen. Since naproxen nitrile was only poorly soluble in water media amended with different water-immiscible organic phases were used for the enrichments. With pristane (2,6,10,14-tetramethylpentadecane) as the organic phase two bacterial strains were isolated (strain C3II and strain MP50) which were identified as rhodococci. Cells of both strains converted naproxen nitrile via naproxen amide to naproxen. From racemic naproxen nitrile Rhodococcus sp. C3II formed S-naproxen amide and subsequently S-naproxen. Racemic naproxen amide was hydrolysed to S-naproxen. Rhodococcus sp. MP50 converted racemic naproxen nitrile predominantly to R-naproxen amide and racemic naproxen amide to S-naproxen. With both strains racemic naproxen amide was converted to S-naproxen with an enantiomeric excess > 99% at a conversion rate up to 80% of the theoretical value. In strain C3II the enzymes which hydrolysed naproxen nitrile and naproxen amide were present only at a low constitutive level. In contrast, in Rhodococcus sp. MP50 these activities were induced when grown in the presence of various nitriles.
Layh
N
N
Institut für Mikrobiologie der Universität Stuttgart, Germany.
Stolz
A
A
Böhme
J
J
Effenberger
F
F
Knackmuss
H J
HJ
D000577:Amides / Q000378:metabolism; D006868:Hydrolysis; D009288:Naproxen / Q000378:metabolism*; D009570:Nitriles / Q000378:metabolism; D012240:Rhodococcus / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000577:Amides; D009570:Nitriles; D009288:Naproxen