Abstract
Pseudomonas putida CGMCC3830 harboring nitrilase was used in isonicotinic acid production from 4-cyanopyridine. This nitrilase showed optimum activities towards 4-cyanopyridine at pH 7.5 and 45°C. The half-life of P. putida nitrilase was 93.3 h, 33.9 h, and 9.5 h at 30°C, 38°C, and 45°C, respectively. 4-Cyanopyridine (100 mM) was fully converted into isonicotinic acid within 20 min. The bench-scale production of isonicotinic acid was carried out using 3 mg of resting cells per mL in a 1 L system at 30°C and finally, 123 g L−1 of isonicotinic acid were obtained within 200 min without any by-products. The conversion reaction suffered from the product inhibition effect after the tenth feeding. The volumetric productivity was 36.9 g L−1 h−1. P. putida shows significant potential in nitrile hydrolysis for isonicotinic acid production. This paper is the first report on isonicotinic acid biosynthesis using Pseudomonas putida and it represents the highest isonicotinic acid production reported so far.
[1] Arai, M., Alavi, Y. I. H., Mendoza, J., Billker, O., & Sinden, R. E. (2004). Isonicotinic acid hydrazide: an antituberculosis drug inhibits malarial transmission in the mosquito gut. Experimental Parasitology, 106, 30–36. DOI: 10.1016/j.exppara.2004.01.002. http://dx.doi.org/10.1016/j.exppara.2004.01.00210.1016/j.exppara.2004.01.002Search in Google Scholar
[2] Banerjee, A., Kaul, P., & Banerjee, U. C. (2006). Enhancing the catalytic potential of nitrilase from Pseudomonas putida for stereoselective nitrile hydrolysis. Applied Microbiology and Biotechnology, 72, 77–87. DOI: 10.1007/s00253-005-0255-8. http://dx.doi.org/10.1007/s00253-005-0255-810.1007/s00253-005-0255-8Search in Google Scholar
[3] Chaplin, J. A., Levin, M. D., Morgan, B., Farid, N., Li, J., Zhu, Z., McQuaid, J., Nicholson, L. W., Rand, C. A., & Burk, M. J. (2004). Chemoenzymatic approaches to the dynamic kinetic asymmetric synthesis of aromatic amino acids. Tetrahedron: Asymmetry, 15, 2793–2796. DOI: 10.1016/j.tetasy.2004.07.060. http://dx.doi.org/10.1016/j.tetasy.2004.07.06010.1016/j.tetasy.2004.07.060Search in Google Scholar
[4] Gong, J. S., Lu, Z. M., Li, H., Shi, J. S., Zhou, Z. M., & Xu, Z. H. (2012). Nitrilases in nitrile biocatalysis: recent progress and forthcoming research. Microbial Cell Factories, 11, 142. DOI: 10.1186/1475-2859-11-142. http://dx.doi.org/10.1186/1475-2859-11-14210.1186/1475-2859-11-142Search in Google Scholar
[5] Kiziak, C., Conradt, D., Stolz, A., Mattes, R., & Klein, J. (2005). Nitrilase from Pseudomonas fluorescens EBC191: cloning and heterologous expression of the gene and biochemical characterization of the recombinant enzyme. Microbiology, 151, 3639–3648. DOI: 10.1099/mic.0.28246-0. http://dx.doi.org/10.1099/mic.0.28246-010.1099/mic.0.28246-0Search in Google Scholar
[6] Kumar, V., & Bhalla, T. C. (2013). Transformation of p-hydroxybenzonitrile to p-hydroxybenzoic acid using nitrilase activity of Gordonia terrae. Biocatalysis and Biotransformation, 31, 42–48. DOI: 10.3109/10242422.2012.757761. http://dx.doi.org/10.3109/10242422.2012.75776110.3109/10242422.2012.757761Search in Google Scholar
[7] Layh, N., Parratt, J., & Willetts, A. (1998). Characterization and partial purification of an enantioselective arylacetonitrilase from Pseudomonas fluorescens DSM 7155. Journal of Molecular Catalysis B: Enzymatic, 5, 467–474. DOI: 10.1016/s1381-1177(98)00075-7. http://dx.doi.org/10.1016/S1381-1177(98)00075-710.1016/S1381-1177(98)00075-7Search in Google Scholar
[8] Maksimova, Yu. G., Vasilyev, D. M., Ovechkina, G. V., Maksimov, A. Yu., & Demakov, V. A. (2013). Transformation of 2- and 4-cyanopyridines by free and immobilized cells of nitrile-hydrolyzing bacteria. Applied Biochemistry and Microbiology, 49, 347–351. DOI: 10.1134/s000368381304008x. http://dx.doi.org/10.1134/S000368381304008X10.1134/S000368381304008XSearch in Google Scholar
[9] Malandra, A., Cantarella, M., Kaplan, O., Vejvoda, V., Uhnáková, B., Štěpáková, B., Kubáč, D., & Martínková, L. (2009). Continuous hydrolysis of 4-cyanopyridine by nitrilases from Fusarium solani O1 and Aspergillus niger K10. Applied Microbiology and Biotechnology, 85, 277–284. DOI: 10.1007/s00253-009-2073-x. http://dx.doi.org/10.1007/s00253-009-2073-x10.1007/s00253-009-2073-xSearch in Google Scholar PubMed
[10] Martínková, L., & Křen, V. (2010). Biotransformations with nitrilases. Current Opinion in Chemical Biology, 14, 130–137. DOI: 10.1016/j.cbpa.2009.11.018. http://dx.doi.org/10.1016/j.cbpa.2009.11.01810.1016/j.cbpa.2009.11.018Search in Google Scholar PubMed
[11] Sharma, N., Sharma, M., & Bhalla, T. (2012). Nocardia globerula NHB-2 nitrilase catalysed biotransformation of 4-cyanopyridine to isonicotinic acid. AMB Express, 2, 25. DOI: 10.1186/2191-0855-2-25. http://dx.doi.org/10.1186/2191-0855-2-2510.1186/2191-0855-2-25Search in Google Scholar PubMed PubMed Central
[12] Vejvoda, V., Kaplan, O., Kubáč, D., Křen, V., & Martínková, L. (2006). Immobilization of fungal nitrilase and bacterial amidase — two enzymes working in accord. Biocatalysis and Biotransformation, 24, 414–418. DOI: 10.1080/10242420601033910. http://dx.doi.org/10.1080/1024242060103391010.1080/10242420601033910Search in Google Scholar
[13] Zhu, X. Y., Gong, J. S., Li, H., Lu, Z. M., Zhou, Z. M., Shi, J. S., & Xu, Z. H. (2013a). Screening, identification and culture optimization of a newly isolated aromatic nitrilaseproducing bacterium — Pseudomonas putida CGMCC3830. Chinese Journal of Biotechnology, in press. Search in Google Scholar
[14] Zhu, X. Y., Gong, J. S., Li, H., Lu, Z. M., Zhou, Z. M., Shi, J. S., & Xu, Z. H. (2013b). Characterization and functional cloning of an aromatic nitrilase from Pseudomonas putida CGMCC3830 with high conversion efficiency toward cyanopyridine. Journal of Molecular Catalysis B: Enzymatic, 97, 175–183. DOI: 10.1016/j.molcatb.2013.08.012. http://dx.doi.org/10.1016/j.molcatb.2013.08.01210.1016/j.molcatb.2013.08.012Search in Google Scholar
© 2013 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
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Articles in the same Issue
- Rapid determination of fosetyl-aluminium in commercial pesticide formulations by high-performance liquid chromatography
- Immobilisation of acid pectinase on graphene oxide nanosheets
- Bench-scale biosynthesis of isonicotinic acid from 4-cyanopyridine by Pseudomonas putida
- Enzymatic synthesis of a chiral chalcogran intermediate
- Separation of Cd(II) and Ni(II) ions by supported liquid membrane using D2EHPA/M2EHPA as mobile carrier
- Fouling of nanofiltration membranes used for separation of fermented glycerol solutions
- Oxyhumolite influence on adsorption and desorption of phosphate on blast furnace slag in the process of two-stage selective adsorption of Cu(II) and phosphate
- Cellulose-precipitated calcium carbonate composites and their effect on paper properties
- Landfill leachate treatment using the sequencing batch biofilm reactor method integrated with the electro-Fenton process
- Effect of sintering temperature on the magnetic properties and charge density distribution of nano-NiO
- Synthesis, optimization, characterization, and potential agricultural application of polymer hydrogel composites based on cotton microfiber
- Cu(II) removal enhancement from aqueous solutions using ion-imprinted membrane technique
- Synthesis of new eburnamine-type alkaloid via direct hydroalkoxylation
- Selection of surfactants as main components of ecological wetting agent for effective extinguishing of forest and peat-bog fires
- Ultrasonic and Lewis acid ionic liquid catalytic system for Kabachnik-Fields reaction
- A simple method for creating molecularly imprinted polymer-coated bacterial cellulose nanofibers
- Determination of pK a of N-alkyl-N,N-dimethylamine-N-oxides using 1H NMR and 13C NMR spectroscopy