Synthesis of Nitroanilines Catalyzed by Horseradish Peroxidase in the Presence of NaNO2 and H2O2

doi:10.1007/s40242-013-3251-z

Abstract

Abstract:

The synthesis of nitroanilines catalyzed by horseradish peroxidase(HRP) in the presence of sodium nitrite and hydrogen peroxide was investigated. o-Nitroaniline and p-nitroaniline were found in the nitrated products. 2-Aminotoluene and 4-aminotoluene could also be nitrated to give corresponding nitrated products. This protocol has great potentials to open new avenues useful for the synthesis of nitroaniline and its derivatives.

Key words: Nitroaniline, Horseradish peroxidase, Phenylamine, Nitration, Enzyme

LIU Cong, DAI Rong-ji, LIN Jie, SUN Jian-hua, CHEN Shi, DENG Yu-lin. Synthesis of Nitroanilines Catalyzed by Horseradish Peroxidase in the Presence of NaNO₂ and H₂O₂[J]. Chemical Research in Chinese Universities, 2013, 29(6): 1164-1166.

References

[1] Li H. M., Nicell J. A., Bioresour. Technol., 2008, 99, 4428
[2] van Deurzen M. P. J., van Rantwijk F., Sheldon R. A., Tetrahedron, 1997, 53, 13183
[3] Chen J., Hong S. S., An Y., Jiang G. Z., Zhang B. X., Fang X. Y., Liu L. Y., Teng L. R., Chem. Res. Chinese Universities, 2007, 23(3), 325
[4] Wang C., Wan P., Gong P. S., Lu L. M., Xu Y. W., Zhao Y., He B., Zhao G., Yan G. L., Mu Y., Lu S. W., Luo G. M., Chem. Res. Chinese Universities, 2011, 27(5), 813
[5] Adam W., Lazarus M., Saha-Moller C. R., Weichold O., Hoch U., Haring D., Schreier P., Adv. Biochem. Eng./Biotechnol., 1999, 63, 73
[6] Colonna S., Gaggero N., Richelmi C., Pasta P., Trends Biotechnol., 1999, 17, 163
[7] Budde C. L., Beyer A., Munir I. Z., Dordick J. S., Khmelnitsky Y. L., J. Mol. Catal. B, Enzym., 2001, 15, 55
[8] Ferrer I., Dezotti M., Duran N., Biotechnol. Lett., 1991, 13, 577
[9] Klibanov A. M., Tu T. M., Scott K. P., Science, 1983, 221, 259
[10] Paice M. G., Jurasek L., Biotechnol. Bioeng., 1984, 26, 477
[11] Ryan B. J., Carolan N., O'fagain C., Trends Biotechnol., 2006, 24, 355
[12] Mceldoon J. P., Dordick J. S., Biotechnol. Prog., 1996, 12, 555
[13] Kamal J. K. A., Behere D. V., Biochem. Eng. J., 2008, 38, 110
[14] Ingram D. T., Lamichhane C. M., Rollins D. M., Carr L. E., Mallinson E. T., Joseph S. W., Clin. Diagn. Lab. Immunol., 1998, 5, 567
[15] Iwuoha E. I., Joseph S., Zhang Z., Smyth M. R., Fuhr U., Ortiz D., Montellano P. R., J. Pharm. Biomed. Anal., 1998, 17, 1101
[16] Ramos M. C., Torijas M. C., Diaz A. N., Sens. Actuators, B, 2001, B73, 71
[17] Zheng L., Jiang F. H., Ma G. R., Zhuang Q. F., Li F., Chem. Res. Chinese Universities, 2011, 27(5), 875
[18] Li Y. X., Zhu L. D., Zhu G. Y., Zhao C., Chem. Res. Chinese Universities, 2002, 18(1), 12
[19] Sheng D., Joshi D. K., Gold M. H., Arch. Biochem. Biophys., 1998, 352, 121
[20] Manini P., Camera E., Picardo M., Napolitano A., D'ischia M., Chem. Phys. Lipids., 2008, 151, 51
[21] Ricoux R., Boucher J. L., Mansuy D., Mahy J. P., Eur. J. Biochem., 2001, 268, 3783

Synthesis of Nitroanilines Catalyzed by Horseradish Peroxidase in the Presence of NaNO₂ and H₂O₂

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	HE Xiaodong, ZHU Jianling, YIN Lunxiang, XIE Bao, LI Kechang, LI Yanqin. Novel Small Four-armed Molecules with Triphenylamine-bridged Structure for Organic Solar Cells Featuring High Open-circuit Voltage [J]. Chemical Research in Chinese Universities, 2019, 35(6): 1032-1039.
[2]	CAO Jing, WANG Miao, CHEN Weihua, SHE Yongxin, WANG Jing, WANG Fengzhong, LAO Shuibing. Artificial Esterase Based on Self-assembly Gel Microspheres Constructed from Chitosan and Amino Acids [J]. Chemical Research in Chinese Universities, 2019, 35(3): 504-508.
[3]	REN Hejun, MA Taigang, ZHAO Jian, ZHOU Rui. V_c-Functionalized Fe₃O₄ Nanocomposites as Peroxidase-like Mimetics for H₂O₂ and Glucose Sensing [J]. Chemical Research in Chinese Universities, 2018, 34(2): 260-268.
[4]	LI Yuwei, BU Mingwei, CHEN Peng, LI Xiaohong, CHEN Changwu, GAO Gui, FENG Yan, HAN Weiwei, ZHANG Zuoming. Characterization of a Thermophilic Monosaccharide Stimulated β-Glucosidase from Acidothermus cellulolyticus [J]. Chemical Research in Chinese Universities, 2018, 34(2): 212-220.
[5]	SU Ping, CHEN Xiaonan, HE Zhangjing, YANG Yi. Preparation of Polyclonal Antibody and Development of a Biotin-streptavidin-based ELISA Method for Detecting Kanamycin in Milk and Honey [J]. Chemical Research in Chinese Universities, 2017, 33(6): 876-881.
[6]	SUN Weizhi, YU Shitao, XIAN Mo. A Green and Efficient Trinitration System for Aromatic Compounds with Bi(NO₃)₃·5H₂O/[HMIM]ClO₄ as Catalyst in HNO₃/Ac₂O [J]. Chemical Research in Chinese Universities, 2015, 31(5): 761-765.
[7]	SHEN Na, YAN Fei, LÜ Shaowu, YANG Wenkui, LUO Guimin, YAN Ganglin, MU Ying. Gene Manipulation Based Selenium-containing Peptide Exhibiting Synergism of SOD and GPx [J]. Chemical Research in Chinese Universities, 2014, 30(6): 947-952.
[8]	ZHOU Xiao-li, HAN Wei-wei, ZHENG Bai-song, FENG Yan. Insight into Substrate Preference of Two Chimeric Esterases by Combining Experiment and Molecular Simulation [J]. Chemical Research in Chinese Universities, 2013, 29(3): 533-537.
[9]	ZHAO Guang-rong, TIAN Li-li, MA Qiong, WANG Chang-song, QIAO Bin, ZHANG Jun-gang, JI Xiang-wu. Peroxynitrite Scavenging Activities of Resveratrol and Piceid [J]. Chemical Research in Chinese Universities, 2012, 28(6): 953-956.
[10]	LI Rong, ZHANG Fei, CAO Shu-gui, XIE Gui-qiu, GAO Ren-jun. Expression and Characterization of a Thermostable Acyl-peptide Releasing Enzyme ST0779 from Sulfolobus tokodaii [J]. Chemical Research in Chinese Universities, 2012, 28(5): 851-855 .
[11]	REN He-jun, LU Yang, ZHOU Rui, DAI Chun-yan, WANG Yan, ZHANG Lan-ying . Molecular Cloning and Characterization of a New Cold-active Extradiol Dioxygenase from a Metagenomic Library Derived from Polychlorinated Biphenyl-contaminated Soil [J]. Chemical Research in Chinese Universities, 2012, 28(4): 666-671.
[12]	LI Xue, WU Yun-jian, LI Zhuo, CHU Wen-ting, ZHANG Hong-xing, ZHENG Qing-chuan. Theoretical Study on GSH Activation Mechanism of a New Type of Glutathione Transferase Gtt2 [J]. Chemical Research in Chinese Universities, 2012, 28(3): 500-502.
[13]	QIAO Wen-qiang. Design, Synthesis and Electrochromic Properties of Anthraquinone Imide-based Donor-acceptor Type of Near Infrared Chromophores [J]. Chemical Research in Chinese Universities, 2012, 28(2): 239-241 .
[14]	Lü Hai-jun, LI Xiang-gao, WANG Shi-rong, GAO Wen-zheng, WANG Sha-sha. Synthesis and Properties of Novel Luminescent Compounds Containing Triphenylamine and Bipyridine Units [J]. Chemical Research in Chinese Universities, 2012, 28(2): 313-318 .
[15]	SUN Yang, HUANG Da-wei, LI Xiao-hui, HU Jian-en, XIU Zhi-long. Microwave-assisted Solid-phase Synthesis, Biological Evaluation and Molecular Docking of Angiotensin I-converting Enzyme Inhibitors [J]. Chemical Research in Chinese Universities, 2012, 28(1): 108-113.