Abstract
The nitrilase from Rhodococcus sp. CCZU10-1 catalyses the hydrolysis of dinitriles to acids without the formation of amides and cyanocarboxylic acids. It was induced by benzonitrile and its analogues (tetrachloroterephthalonitrile > ε-caprolactam > benzonitrile > phenylacetonitrile), and had activity towards aromatic nitriles (terephthalonitrile > tetrachloroterephthalonitrile > isophthalonitrile > tetrachloroisophthalonitrile > tetrafluoroterephthalonitrile > benzonitrile). After the optimization, the highest nitrilase induction [311 U/(g DCW)] was achieved with tetrachloroterephthalonitrile (1 mM) in the medium after 24 h at 30 °C after optimum enzyme activity was at pH 6.8 and at 30 °C. Efficient biocatalyst recycling was achieved by cell immobilization in calcium alginate, with a product-to-biocatalyst ratios of 776 g terephthalic acid/g DCW and 630 g isophthalic acid/g DCW.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Banerjee A, Kaul P, Banerjee UC (2006) Enhancing the catalytic potential of nitrilase from Pseudomonas putida for stereoselective nitrile hydrolysis. Appl Microbiol Biotechnol 72:77–87
Bayer S, Birkemeyer C, Ballschmiter M (2011) A nitrilase from a metagenomic library acts regioselectively on aliphatic dinitriles. Appl Microbiol Biotechnol 89:91–98
Bengis-Garber C, Gutman AL (1989) Selective hydrolysis of dinitriles into cyano-carboxylic acids by Rhodococcus rhodochrous N.C.I.B. 11216. Appl Microbiol Biotechnol 32:11–16
Bramucci MG, McCutchen CM, Nagarajan V, Thomas SM (2001) Microbial production of terephthalic acid and isophthalic acid. US Patent 6,187,569
Cowan D, Cramp R, Pereira R, Graham D, Almatawah Q (1998) Biochemistry and biotechnology of mesophilic and thermophilic nitrile metabolizing enzymes. Extremophiles 2:207–216
Gavagan JE, DiCosimo R, Eisenberg A, Fager SK, Folsom PW, Hann EC, Schneider KJ, Fallon RD (1999) A Gram-negative bacterium producing a heat-stable nitrilase highly active on aliphatic dinitriles. Appl Microbiol Biotechnol 52:654–659
He YC, Xu JH, Su JH, Zhou L (2010) Bioproduction of glycolic acid from glycolonitrile with a new bacterial isolate of Alcaligenes sp. ECU0401. Appl Biochem Biotechnol 37:741–750
He YC, Zhou Q, Ma CL, Cai ZQ, Wang LQ, Zhao XY, Chen Q, Gao DZ, Zheng M, Wang XD, Sun Q (2012) Biosynthesis of benzyolformic acid from benzyol cyanide by a newly isolated Rhodococcus sp. CCZU10-1 in toluene-water biphasic system. Bioresour Technol 115:88–95
Kobayashi M, Nagasawa T, Yamada H (1988) Regiospecific hydrolysis of dinitrile compounds by nitrilase from Rhodococcus rhodochrous J1. Appl Microbiol Biotechnol 29:231–233
Vejvoda V, Sveda O, Kaplan O, Prikrylová V, Elisáková V, Himl M, Kubác D, Pelantová H, Kuzma M, Kren V, Martínková L (2007) Biotransformation of heterocyclic dinitriles by Rhodococcus erythropolis and fungal nitrilases. Biotechnol Lett 29:1119–1124
Wang J, Tian J, Xu JH (2006) A method for producing terephthalic acid by Comamonas testosterone DSM6577. Chin J Catal 27:297–298
Yeom SJ, Kim HJ, Lee JK, Kim DE, Oh DK (2008) An amino acid at position 142 in nitrilase from Rhodococcus rhodochrous ATCC 33278 determines the substrate specificity for aliphatic and aromatic nitriles. Biochem J 415:401–407
Acknowledgments
This work was financially supported by the National Natural Science Foundation of China (No. 21102011).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
He, YC., Wu, YD., Pan, XH. et al. Biosynthesis of terephthalic acid, isophthalic acid and their derivatives from the corresponding dinitriles by tetrachloroterephthalonitrile-induced Rhodococcus sp.. Biotechnol Lett 36, 341–347 (2014). https://doi.org/10.1007/s10529-013-1367-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10529-013-1367-3