Abstract
Pyridine and its heterocyclic derivatives are widely encountered in industrial wastewaters, and they are relatively recalcitrant to biodegradation. Pyridine biodegradation is initiated by two mono-oxygenation reactions that compete for intracellular electron donor (2H). In our experiments, UV photolysis of pyridine generated succinate, whose oxidation augmented the intracellular electron donor and accelerated pyridine biodegradation and mineralization. The first mono-oxygenation reaction always was faster than the second one, because electrons provided by intracellular electron donors were preferentially utilized by the first mono-oxygenase; this was true even when the concentration of 2HP was greater than the concentration of pyridine. In addition, the first mono-oxygenation had faster kinetics because it had higher affinity for its substrate (pyridine), along with less substrate self-inhibition.
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References
Aiba S, Shoda M, Nagalani M (2000) Kinetics of product inhibition in alcohol fermentation. Biotechnol Bioeng 67(6):671–690
Arjomandi-Behzad L, Yamini Y, Rezazadeh M (2014) Extraction of pyridine derivatives from human urine using electromembrane extraction coupled to dispersive liquid–liquid microextraction followed by gas chromatography determination. Talanta 126:73–81
Bai Y, Sun Q, Zhao C, Wen D, Tang X (2009) Aerobic degradation of pyridine by a new bacterial strain, Shinella zoogloeoides BC026. J Ind Microbiol Biotechnol 36:1391–1400
Bai Q, Yang L, Li R, Chen B, Zhang L, Zhang Y, Rittmann BE (2015) Accelerating quinoline biodegradation and oxidation with endogenous electron donors. Environ Sci Technol 49(19):11536–11542
Bokhove J, Schuur B, de Haan AB (2012) Solvent design for trace removal of pyridines from aqueous streams using solvent impregnated resins. Sep Purif Technol 98:410–418
Cao L, Sun W, Zhang Y, Feng S, Dong J, Zhang Y, Rittmann BE (2017) Competition for electrons between reductive dechlorination and denitrification. Front Environ Sci Eng. https://doi.org/10.1007/s11783-017-0959-x
Chang L, Zhang Y, Gan L, Xu H, Yan N, Liu R, Rittmann BE (2014) Internal loop photo-biodegradation reactor used for accelerated quinoline degradation and mineralization. Biodegradation 25(4):587–594
Chen B, Song J, Yang L, Bai Q, Li R, Zhang Y, Rittmann BE (2015) Coupling UV-H2O2 to accelerate dimethyl phthalate (DMP) biodegradation and mineralization oxidation. Biodegradation 26(6):431–441
Dahlen EP, Rittmann BE (2002) Two-tank suspended growth process for accelerating the detoxification kinetics of hydrocarbons requiring initial mono-oxygenation reactions. Biodegradation 13(2):101–116
Fent K, Bucheli TD (1995) Inhibition of hepatic microsomal mono-oxygenase system by organotins in fish. Mar Environ Res 39(1–4):351–352
Fetzner S (1998) Bacterial degradation of pyridine, indole, quinolone and their derivatives under different redox conditions. Appl Microbiol Biotechnol 49(3):237–250
Li J, Cai W, Cai J (2009) The characteristics and mechanisms of pyridine biodegradation by streptomyces sp. J Hazard Mater 165:950–954
Li N, Lu X, Zhang S (2014) A novel reuse method for waste printed circuit boards as catalyst for wastewater bearing pyridine degradation. Chem Eng J 257:253–261
Mohan D, Singh KP, Sinha S, Gosh D (2004) Removal of pyridine from aqueous solution using low cost activated carbons derived from agricultural waste materials. Carbon 42:2409–2421
Padoley KV, Mudliar SN, Banerjee SK, Deshmukh SC, Pandey RA (2011) Fenton oxidation: a pretreatment option for improved biological treatment of pyridine and 3-cyanopyridine plant wastewater. Chem Eng J 166:1–9
Pandey RA, Padoley KV, Mukherji SS, Mudliar SN, Vaidya AN, Rajvaidya AS, Subbarao TV (2007) Biotreatment of waste gas containing pyridine in a biofilter. Bioresour Technol 98:2258–2267
Rehakova M, Fortunova L, Bastl Z, Nagyova S, Dolinska S, Jorik V, Jona E (2011) Removal of pyridine from liquid and gas phase by copper forms of natural and synthetic zeolites. J Hazard Mater 186:699–706
Schmoldt A, Buhr SL, Albersmeyer K (1980) Effects of inducers and inhibitors of rat liver mono-oxygenases on digitoxin metabolism. Biochem Pharmacol 29(3):405–409
Tang Y, Zhang Y, Yan N, Liu R, Rittmann BE (2015) The role of electron donors generated from UV photolysis for accelerating pyridine biodegradation. Biotechnol Bioeng 112(9):1792–1800
Wen D, Zhang J, Xiong R, Liu R, Chen L (2013) Bioaugmentation with a pyridine degrading bacterium in a membrane bioreactor treating pharmaceutical wastewater. J Environ Sci 25:2265–2271
Yan N, Chang L, Gan L, Zhang Y, Liu R, Rittmann BE (2013) UV photolysis for accelerated quinoline biodegradation and mineralization. Appl Microbiol Biotechnol 97(24):10555–10561
Yang L, Zhang Y, Bai Q, Yan N, Xu H, Rittmann BE (2015) Intimately coupling of photolysis accelerates nitrobenzene biodegradation, but sequential coupling slows biodegradation. J Hazard Mater 287:252–258
Zalat OA, Elsayed MA (2013) A study on microwave removal of pyridine from wastewater. J Environ Chem Eng 1:137–143
Zefirov NS, Agapova SR, Terentiev PB, Bulakhova IM, Vasyuk-ova NI, Modyanova LV (1994) Degradation of pyridine by Arthrobacter crystallopoietes and Rhodococcus opacus strains. FEMS Microbiol Lett 118:71–74
Zhang Y, Chang L, Yan N, Tang YT, Liu R, Rittmann BE (2014) UV photolysis for accelerating pyridine biodegradation. Environ Sci Technol 48(1):649–655
Acknowledgements
The authors acknowledge the financial support of the National Natural Science Foundation of China (50978164), the Ability Construction Project of Local Colleges and Universities in Shanghai (16070503000), Special Fund of State Key Joint Laboratory of Environment Simulation and Pollution Control (16K10ESPCT), Shanghai Gaofeng & Gaoyuan Project for University Academic Program Development, and the United States National Science Foundation (0651794).
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Yang, C., Tang, Y., Xu, H. et al. Competition for electrons between mono-oxygenations of pyridine and 2-hydroxypyridine. Biodegradation 29, 419–427 (2018). https://doi.org/10.1007/s10532-018-9834-0
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DOI: https://doi.org/10.1007/s10532-018-9834-0