Biotransformation of aromatic and heterocyclic amides by amidase of whole cells of Rhodococcus sp. MTB5: Biocatalytic characterization and substrate specificity

References

• Agarwal S, Gupta M, Choudhury B. 2013. Bioprocess development for nicotinic acid hydroxamate synthesis by acyltransferase activity of Bacillus smithii strain IITR6b2. J Ind Microbiol Biotechnol 40:937–946.
   PubMed Web of Science ®Google Scholar
• Banerjee A, Sharma R, Banerjee UC. 2002. The nitrile-degrading enzymes: current status and future prospects. Appl Microbiol Biotechnol 60:33–44.
   PubMed Web of Science ®Google Scholar
• Bhatia RK, Bhatia SK, Mehta PK, Bhalla TC. 2013. Bench scale production of benzohydroxamic acid using acyl transfer activity of amidase from Alcaligenes sp. MTCC 10674. J Ind Microbiol Biotechnol 40:21–27.
   PubMed Web of Science ®Google Scholar
• Bhatia RK, Bhatia SK, Mehta PK, Bhalla TC. 2014. Biotransformation of nicotinamide to nicotinyl hydroxamic acid at bench scale by amidase acyl transfer activity of Pseudomonas putida BR-1. J Mol Catal B: Enzym 108:89–95.
   Web of Science ®Google Scholar
• Cantarella M, Cantarella L, Gallifuoco A. 2006. Nitrile bioconversion by Microbacterium imperiale CBS 498-74 resting cells in batch and ultrafiltration membrane bioreactors. J Ind Microbiol Biotechnol 33:208–214.
   PubMed Web of Science ®Google Scholar
• Cantarella M, Cantarella L, Gallifuoco A, Intellini R, Kaplan O, Spera A, Martınkov L. 2008. Amidase-catalyzed production of nicotinic acid in batch and continuous stirred membrane reactors. Enzyme Microb Technol 42:222–229.
   Web of Science ®Google Scholar
• Ciskanik LM, Wilczek JM, Fallon RD. 1995. Purification and characterization of an enantioselective amidase from Pseudomonas chlororaphis B23. Appl Environ Microbiol 61:998–1003.
   PubMed Web of Science ®Google Scholar
• Dadd MR, Claridge TDW, Pettman AJ, Knowles CJ. 2001. Biotransformation of benzonitrile to benzohydroxamic acid by Rhodococcus rhodochrous in the presence of hydroxylamine. Biotechnol Lett 23:221–225.
   Web of Science ®Google Scholar
• Demirjian DC, Morís-Varas F, Cassidy CS. 2001. Enzymes from extremophiles. Curr Opin Chem Biol 5:144–151.
   PubMed Web of Science ®Google Scholar
• Egorova K, Trauthwein H, Verseck S, Antranikian G. 2004. Purification and properties of an enantioselective and thermoactive amidase from the thermophilic actinomycete Pseudonocardia thermophila. Appl Microbiol Biotechnol 65:38–45.
   PubMed Web of Science ®Google Scholar
• Fu L, Li X, Xiao X, Xu J. 2014. Purification and characterization of a thermostable aliphatic amidase from the hyperthermophilic archaeon Pyrococcus yayanosii CH1. Extremophiles 18:429–440.
   PubMed Web of Science ®Google Scholar
• Graham D, Pereira R, Barfield D, Cowan D. 2000. Nitrile biotransformations using free and immobilized cells of a thermophilic Bacillus spp. Enzyme Microb Technol 26:368–373.
   PubMed Web of Science ®Google Scholar
• Hazan R, Levine A, Abeliovich H. 2004. Benzoic Acid, a weak organic acid food preservative, exerts specific effects on intracellular membrane trafficking pathways in Saccharomyces cerevisiae. Appl Environ Microbiol 70:4449–4457.
   PubMed Web of Science ®Google Scholar
• He Y, Xu J, Su J, Zhou L. 2010. Bioproduction of glycolic acid from glycolonitrile with a new bacterial isolate of Alcaligenes sp. ECU0401. Appl Biochem Biotechnol 160:1428–1440.
   PubMed Web of Science ®Google Scholar
• Hirrlinger B, Stolz A, Knackmuss H. 1996. Purification and properties of an amidase from Rhodococcus erythropolis MP50 which enantioselectively hydrolyzes 2-arylpropionamides. J Bacteriol 178:3501–3507.
   PubMed Web of Science ®Google Scholar
• Jin L, Liu Z, Xu J, Zheng Y. 2013. Biosynthesis of nicotinic acid from 3-cyanopyridine by a newly isolated Fusarium proliferatum ZJB-09150. World J Microbiol Biotechnol 29:431–440.
   PubMed Web of Science ®Google Scholar
• Kerridge A, Parratt JS, Roberts SM, Theil F, Turner NJ, Willettsa AJ. 1994. Microbial hydrolysis of glutaronitrile derivatives with Brevibacterium sp. R 312. Bioorg Med Chem 2:447–455.
   PubMedGoogle Scholar
• Makhongela HS, Glowacka AE, Agarkar VB, Sewell BT, Weber B, Cameron RA, Cowan DA, Burton SG. 2007. A novel thermostable nitrilase superfamily amidase from Geobacillus pallidus showing acyl transfer activity. Appl Microbiol Biotechnol 75:801–811.
   PubMed Web of Science ®Google Scholar
• Matar S, Hatch LF. 2000. Chemistry of petrochemical processes. 2nd ed. Houston, TX: Gulf Publishing Company.
   Google Scholar
• Mehta PK, Bhatia SK, Bhatia RK, Bhalla TC. 2014. Bench scale production of nicotinic acid using a versatile amide-hydrolysing Geobacillus subterraneus RL-2a isolated from thermal spring of Manikaran, India. J Mol Catal B: Enzym 105:58–65.
   Web of Science ®Google Scholar
• Mei-Xiang W. 2015. Enantioselective biotransformations of nitriles in organic synthesis. Acc Chem Res 48:602–611.
   PubMed Web of Science ®Google Scholar
• Mukram I, Nayak AS, Kirankumar B, Monisha TR, Reddy PV, Karegoudar TB. 2015. Isolation and identification of a nitrile hydrolyzing bacterium and simultaneous utilization of aromatic and aliphatic nitriles. Int Biodeterior Biodegrad 100:165–171.
   Web of Science ®Google Scholar
• Nampoothiri KM, Roopesh K, Chacko S, Pandey A. 2005. Comparative study of amidase production by free and immobilised Escherichia coli cells. Appl Biochem Biotechnol 120:97–108.
   PubMed Web of Science ®Google Scholar
• Nawaz MS, Khan AA, Seng JE, Leakey JE, Siitonen PH, Cerniglia CE. 1994. Purification and characterization of an amidase from an acrylamide-degrading Rhodococcus sp. Appl Environ Microbiol 60:3343–3348.
   PubMed Web of Science ®Google Scholar
• Nawaz MS, Khan AA, Bhattacharayya D, Siitonen PH, Cerniglia CE. 1996. Physical, biochemical, and immunological characterization of a thermostable amidase from Klebsiella pneumoniae NCTR 1. J Bacteriol 178:2397–2401.
   PubMed Web of Science ®Google Scholar
• Otto M, Mei-Xiang W. 1997. An in-depth study of the biotransformation of nitriles into amides and/or acids using Rhodococcus rhodochrous AJ2701. J Chem Soc Perkin Trans 1:1099–1104.
   Google Scholar
• Pandey D, Singh R, Chand D. 2011. An improved bioprocess for synthesis of acetohydroxamic acid using DTT (dithiothreitol) treated resting cells of Bacillus sp. APB-6. Bioresour Technol 102:6579–6586.
   PubMed Web of Science ®Google Scholar
• Park H, Uhm K, Kim H. 2008. R-Stereoselective amidase from Rhodococcus erythropolis no. 7 acting on 4-chloro-3-hydroxybutyramide. J Microbiol Biotechnol 18:552–559.
   PubMed Web of Science ®Google Scholar
• Prasad S, Sharma DR, Bhalla TC. 2005. Nitrile- and amide- hydrolysing activity in Kluyveromyces thermotolerans MGBY 37. World J Microbiol Biotechnol 21:1447–1450.
   Web of Science ®Google Scholar
• Prasad S, Misra A, Jangir V, Awasthi A, Raj J, Bhalla TC. 2007. A propionitrile-induced nitrilase of Rhodococcus sp. NDB 1165 and its application in nicotinic acid synthesis. World J Microbiol Biotechnol 23:345–353.
   Web of Science ®Google Scholar
• Raj J, Singh N, Prasad S, Seth A, Bhalla TC. 2007. Bioconversion of benzonitrile to benzoic acid using free and agar entrapped cells of Nocardia globerula NHB-2. Acta Microbiol Immunol Hung 54:79–88.
   PubMedGoogle Scholar
• Rahim MA, Saxena RK, Gupta R, Sheoran A, Giri B. 2003. A novel and quick plate assay for acetamidase producers and process optimization for its production by Aspergillus candidus. Process Biochem 38:861–866.
   Web of Science ®Google Scholar
• Ruan L, Zheng R, Zheng Y. 2016. Mining and characterization of two amidase signature family amidases from Brevibacterium epidermidis ZJB-07021 by an efficient genome mining approach. Protein Express Purif 126:16–25.
   PubMed Web of Science ®Google Scholar
• Schär HP, Holzman W, Ramos TGM, Ghisalba O. 1986. Purification and characterization of N,N-dimethylformamidase from Pseudomonas DMF 3/3. Eur J Biochem 158:469–475.
   PubMedGoogle Scholar
• Sharma NN, Sharma M, Bhalla TC. 2009. Amidases: versatile enzymes in nature. Rev Env Sci Biotechnol 8:343–366.
   Google Scholar
• Sharma NN, Sharma M, Bhalla TC. 2011. An improved nitrilase-mediated bioprocess for synthesis of nicotinic acid from 3-cyanopyridine with hyperinduced Nocardia globerula NHB-2. J Ind Microbiol Biotechnol 38:1235–1243.
   PubMed Web of Science ®Google Scholar
• Shaw NM, Naughton A, Robins K, Tinschert A, Schmid E, Hischier M, Venetz V, Werlen J, Zimmermann T, Brieden W, et al. 2002. Selection, purification, characterisation, and cloning of a novel heat-stable stereo-specific amidase from Klebsiellaoxytoca, and its application in the synthesis of enantiomerically pure (R)- and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acids and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. Org Process Res Dev 6:497–504.
   Web of Science ®Google Scholar
• Syed MA, Ahmad SA, Kusnin N, Shukor MYA. 2012. Purification and characterization of amidase from acrylamide-degrading bacterium. Afr J Biotechnol 11:329–336.
   Google Scholar
• Takashi K, Tatsuhiko O. 1990. Purification and properties of an aromatic amidase from Pseudomonas sp. GDI 211. Agr Biol Chem 54:2565–2571.
   Google Scholar
• Trott S, Bauer R, Knackmuss H, Stolz A. 2001. Genetic and biochemical characterization of an enantioselective amidase from Agrobacterium tumefaciens strain d3. Microbiology 147:1815–1824.
   PubMed Web of Science ®Google Scholar
• Wilson CO, Gisvold O, Block JH. 2004. Wilson and Gisvold's Textbook of organic medicinal and pharmaceutical. Philadelphia: Lippincott Williams & Wilkins, p. 234.
   Google Scholar
• Woodley JM. 2006. Choice of biocatalyst form for scalable processes. Biochem Soc Trans 34:301–303.
   PubMed Web of Science ®Google Scholar
• Wu Z, Zheng R, Zheng Y. 2016. Exploitation and characterization of three versatile amidase super family members from Delftia tsuruhatensis ZJB-05174. Enzyme Microb Technol 86:93–102.
   PubMed Web of Science ®Google Scholar
• Yamada H, Shimizu S. 1988. Microbial and enzymatic processes for the production of biologically and chemically useful compounds. Angew Chem Int Ed Engl 27:622–642.
   Web of Science ®Google Scholar
• Yang Z, Nia Y, Lub Z, Liaoa X, Zhengc Y, Suna Z. 2011. Industrial production of S-2,2-dimethylcyclopropanecarboxamide with a novel recombinant R-amidase from Delfti atsuruhatensis. Process Biochem 46:182–187.
   Web of Science ®Google Scholar