The Utilization of Pyridine Carbonitriles and Carboxamides by Nocardia rhodochrous LL100-21

Vaughan, Peter A.; Cheetham, Peter S. J.; Knowles, Christopher J.

doi:10.1099/00221287-134-5-1099

Cited by 11 publications

(7 citation statements)

References 18 publications

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“…Early works demonstrated that both nitrilase and nitrile hydratase/amidase pathways could occur in the same strains, and those enzyme involved were produced selectively by the addition of different inducers, such as Nocardia rhodochrous LL100‐21 [33] and Rhodococcus rhodochrous J1 [34]. Similar results were found in B. subtilis ZJB‐063.…”

Section: Resultsmentioning

confidence: 77%

Biotransformation of p‐methoxyphenylacetonitrile into p‐methoxyphenylacetic acid by resting cells of Bacillus subtilis

Chen

Zheng

Shen

2008

Biotech and App Biochem

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Resting cells of Bacillus subtilis ZJB-063 were used for the direct transformation of MOPAN (p-methoxyphenylacetonitrile) to MOPAA (p-methoxyphenylacetic acid), which is an important pharmaceutical intermediate. The B. subtilis ZJB-063 culture conditions for the production of nitrilase and the reaction conditions for this nitrilase-mediated conversion were optimized. The maximum production of nitrilase was achieved when glucose and a combination of ammonium sulfate and yeast powder were added as carbon and nitrogen sources respectively. Previously reported inducers were found to be unnecessary for the production of nitrilase from B. subtilis ZJB-063, which indicated that this nitrilase appeared to be constitutive. However, when epsilon-caprolactam (6-hexanolactam) was added as the inducer, B. subtilis ZJB-063 exhibited nitrile hydratase and amidase activity. The maximum conversion of MOPAN into MOPAA (specific activity 17.03 units.g(-1)(DCW); DCW is dry cell weight) was observed in a solution containing 50 mM phosphate buffer (pH 7.0), 10 mM MOPAN, 2.7 mg DCW.ml(-1) wet resting cells and 5% (v/v) DMSO for 4 h at 32 degrees C. MOPAN (10 mM) was completely converted into MOPAA (9.65 mM) in 5 h in shake flasks without the formation of p-methoxyphenylacetamide. The small deviation of MOPAA (9.65 mM) from the theoretical amount (10 mM) may be due to partial consumption of the products by B. subtilis ZJB-063. Both MOPAN and MOPAA inhibited the hydrolysis at concentrations above 15 mM. Scale up of the reaction to 200 ml in a bubble bioreactor shortened the reaction time compared with the reactions performed in shake flasks.

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Section: Resultsmentioning

confidence: 77%

Biotransformation of p‐methoxyphenylacetonitrile into p‐methoxyphenylacetic acid by resting cells of Bacillus subtilis

Chen

Zheng

Shen

2008

Biotech and App Biochem

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“…Vaughan et al (132) reported that 3-cyanopyridine (3-pyridine-carbonitrile) was hydrolyzed to nicotinic acid and ammonium by Nocardia rhodochrous. Ammonium was utilized for growth, whereas nicotinic acid was not further metabolized.…”

Section: Transformation Of Other Pyridine Derivatives Nitrogen Substimentioning

confidence: 99%

Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions.

Kaiser

Feng

Bollag

1996

Microbiological Reviews

185

131

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“…Generally both groups of enzymes show a wide substrate range. Nitrilases usually are active with aromatic nitriles, but exhibit no or only marginal activity with aliphatic nitriles (Harper 1977a, b;Vaughan et al 1988;Nagasawa et al 1988b;Kobayashi et al 1989). In contrast nitrile hydratases prefer aliphatic nitriles as substrates (Maestracci et al 1984;Nagasawa et al 1987;Watanabe et al 1987;Nagasawa et al 1988a;Endo and Watanabe, 1989;Tani et al 1989).…”

Section: Discussionmentioning

confidence: 99%

Enantioselective hydrolysis of O-acetylmandelonitrile to O-acetylmandelic acid by bacterial nitrilases

et al. 1992

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The Utilization of Pyridine Carbonitriles and Carboxamides by Nocardia rhodochrous LL100-21

Cited by 11 publications

References 18 publications

Biotransformation of p‐methoxyphenylacetonitrile into p‐methoxyphenylacetic acid by resting cells of Bacillus subtilis

Biotransformation of p‐methoxyphenylacetonitrile into p‐methoxyphenylacetic acid by resting cells of Bacillus subtilis

Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions.

Enantioselective hydrolysis of O-acetylmandelonitrile to O-acetylmandelic acid by bacterial nitrilases

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