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

Layh, Norman; Stolz, A.; Förster, Siegfried; Effenberger, Franz; Knackmuss, Hans‐Joachim

doi:10.1007/bf00276300

Cited by 60 publications

(20 citation statements)

References 37 publications

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“…The enzymatic hydrolysis of nitriles represents a very convenient synthetic method for amides and/or carboxylic acids due to the mild reaction conditions. Furthermore, these enzymatic reactions also allow the enantioselective synthesis of optical active amides and carboxylic acids from racemic precursors (Mayaux et al, 1990(Mayaux et al, , 1991Yamamoto et al, 1990;Kakeya et al, 1991;Bianchi et al, 1991;Bhalla et al, 1992;Cohen et al, 1992;Layh et al, 1992).…”

Section: Discussionmentioning

confidence: 99%

“…Naphthalene-2-carbonitrile and 2-naphthalenecarboxamide were purchased from Lancaster Synthesis (Eastgate, UK) and naphthalene-2-carboxylic acid from Fluka (Buchs, Switzerland). All other culture media, chemicals and apparatus were the same as described before (Layh et al, 1992).…”

Section: Chemicalsmentioning

confidence: 99%

“…Bacterial cultures were grown in a nitrogenfree mineral medium according to Layh et al (1992) with succinate (10 mM) as sole source of carbon and energy. Naproxen nitrile was added as sole source of nitrogen.…”

Section: Mediamentioning

confidence: 99%

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Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates

Layh

Stolz

Böhme

et al. 1994

Journal of Biotechnology

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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.

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Section: Discussionmentioning

confidence: 99%

Section: Chemicalsmentioning

confidence: 99%

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Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates

Layh

Stolz

Böhme

et al. 1994

Journal of Biotechnology

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“…Bacteria were isolated from soil sample by an enrichment culture procedure (Layh et al 1992). Enrichments were carried out in the nitrogen-free minimal medium containing 2 g of acetamide as nitrogen source (Pal and Samanta 1999).…”

Section: Chemicalsmentioning

confidence: 99%

Biotransformation of amide using Bacillus sp.: isolation strategy, strain characteristics and enzyme immobilization

Sogani

Mathur

Bhatnagar

et al. 2011

Int. J. Environ. Sci. Technol.

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Amidase hydrolases/acyltransferases are of considerable industrial interest due to potential applications in the production of useful hydroxamic acids. The test strain, capable of acetamide degradation, was isolated by an enrichment technique with acetamide as sole source of nitrogen. Based on morphology, physiological tests and biochemical tests, this isolate was identified as Bacillus sp. and on the basis of 16S Ribosomal ribonucleic acid sequence, a phylogenetic tree was drawn and was identified as Bacillus megaterium. Resting cells containing active acyltransferase enzyme were prepared and immobilized in the gel beads of sodium alginate, agar, polyacrylamide and polyvinyl alcohol-alginate. The beads were tested for acyltransferase using Iron (III) chloride reagents at 55°C and were found to be affected by substrate concentration, type of buffer, buffer pH and reaction temperature. These factors were optimized using sodium alginate immobilized beads. This study proved useful in understanding the technique of immobilization of acyltransferase enzyme, its operational stability and its importance in the synthesis of hydroxamic acid.

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“…Recently attention has been directed towards regio-and/or stereoselective nitrile hydrolysis by, for example, Brevibacterium imperiale B222 (4), Pseudomonas spp. (15).…”

Section: Introductionmentioning

confidence: 99%

Biodegradation of acetonitrile by cells of Candida guilliermondii UFMG-Y65 immobilized in alginate, kappa-carrageenan and citric pectin

Dias¹,

Rezende²,

Linardi³

2000

Braz. J. Microbiol.

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Different encapsulation matrices were tested for immobilized cells of Candida guilliermondii UFMG-Y65 used for acetonitrile degradation. Acetonitrile degradation by free cells and cells immobilized in Ba-alginate, κ-carrageenan and citric pectin was studied. The rate of acetonitrile degradation was monitored for 120 h by measuring yeast growth and ammonia concentration. Different alginate concentrations did not affect cell viability, but the period of incubation in BaCl 2 solution reduced the number of viable cells. Likewise, the gel nature and the matrix structure of the support resulting from the cell immobilization conditions were of fundamental importance for biocatalyst activity and performance, affecting substantially the patterns of microbial growth and enzymatic activity. Alginate-immobilized cells degraded acetonitrile more efficiently than κ-carrageenan or citric pectin-immobilized cells.

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

Abstract: Abstract. Bacteria were enriched from soil samples, using benzylcyanide, a-methyl-, c~-ethyl-or c~-methoxybenzylcyanide as the sole source of nitrogen. All isolated strains

Cited by 60 publications

References 37 publications

Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates

Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates

Biotransformation of amide using Bacillus sp.: isolation strategy, strain characteristics and enzyme immobilization

Biodegradation of acetonitrile by cells of Candida guilliermondii UFMG-Y65 immobilized in alginate, kappa-carrageenan and citric pectin

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