Biomimetic synthesis of 1-aryl-2,5-dimethyl pyrroles using egg white nano-ovalbumin at room temperature under solvent-free conditions
محورهای موضوعی : Iranian Journal of CatalysisNaeimeh Salehi 1 , Bi Bi Fatemeh Mirjalili 2
1 - Department of Chemistry, College of Science, Yazd University, Yazd, P. O. Box 89195-741, I. R. Iran.
2 - Department of Chemistry, College of Science, Yazd University, Yazd, P. O. Box 89195-741, I. R. Iran.
کلید واژه: Biocatalyst, N-substituted pyrroles, Egg white nano-ovalbumin, Paal-Knorr reaction,
چکیده مقاله :
Ovalbumin, as the major component of egg-white, is a globular, biocompatible, nontoxic and biodegradable phosphoglyco protein. This protein with the molecular weight of 44.5 kDa, contains 385 residues of amino acids with isoelectric point (pI) of 4.5. Many purification procedures have been reported for egg-white proteins such as gel permeation and anion exchange chromatography. In this study, we have reported a new inexpensive protocol using acetic acid and sodium chloride for extraction and purification of egg white nano-ovalbumin. The effective performance of this protein as a biocatalyst was proved through synthesis of N-substituted pyrrole derivatives. This reported innovative biomethodology has some advantages such as less pollution, mild reaction conditions, reusability of biocatalyst and excellent yields.
[1] G. Boucher, S. Robin, V. Fargeas, T. Dintinger, M. Mathé‐Allainmat, J. Lebreton, C. Tellier, ChemBioChem. 6 (2005) 807-810.
[2] M.T. Reetz, R. Mondiere, J.D. Carballeira, Tetrahedron Lett. 48 (2007) 1679-1681.
[3] F. Benedetti, F. Berti, S. Bidoggia, Org. Biomol. Chem. 9 (2011) 4417-4420.
[4] E. Busto, V. Gotor-Fernández, V. Gotor, Org. Process Res. Dev. 15 (2010) 236-240.
[5] N. Gaggero, D.C.M. Albanese, G. Celentano, S. Banfi, A. Aresi, Tetrahedron: Asymmetry 22 (2011) 1231-1233.
[6] F. Berti, S. Bincoletto, I. Donati, G. Fontanive, M. Fregonese, F. Benedetti, Org. Biomol. Chem. 9 (2011) 1987-1999.
[7] D.-D. Zhao, L. Li, F. Xu, Q. Wu, X.-F. Lin, J. Mol. Catal B: Enzym. 95 (2013) 29-35.
[8] U.K. Sharma, N. Sharma, R. Kumar, A.K. Sinha, Amino Acids 44 (2013) 1031-1037.
[9] A.C.C. Alleoni, Sci. Agric. (Piracicaba, Braz.) 63 (2006) 291-298.
[10] A. Tankrathok, S. Daduang, R. Patramanon, T. Araki, S. Thammasirirak, Prep. Biochem. Biotechnol. 39 (2009) 380-399.
[11] M. Vachier, M. Piot, A. Awade, J. Chromatogr. B: Biomed. Sci. Appl. 664 (1995) 201-210.
[12] H. Chick, C.J. Martin, Biochem. J. 7 (1913) 380-398.
[13] T. Croguennec, F. Nau, S. Pezennec, G. Brule, J. Agric. Food Chem. 48 (2000) 4883-4889.
[14] W.W. Wilkerson, R.A. Copeland, M. Covington, J.M. Trzaskos, J. Med. Chem. 38 (1995) 3895-3901.
[15] R.P. Wurz, A.B. Charette, Org. Lett. 7 (2005) 2313-2316.
[16] H. Lee, J. Lee, S. Lee, Y. Shin, W. Jung, J.-H. Kim, K. Park, K. Kim, H.S. Cho, S. Ro, Bioorg. Med. Chem. Lett. 11 (2001) 3069-3072.
[17] C.Y. de Leon, B. Ganem, Tetrahedron 53 (1997) 7731-7752.
[18] C. Paal, Ber. Dtsch. Chem. Ges. 18 (1885) 367-371.
[19] A. Rahmatpour, Monatsh. Chem. 143 (2012) 491-495.
[20] H. Veisi, Tetrahedron Lett. 51 (2010) 2109-2114.
[21] B.K. Banik, I. Banik, M. Renteria, S.K. Dasgupta, Tetrahedron Lett. 46 (2005) 2643-2645.
[22] J.-X. Chen, M.-C. Liu, X.-L. Yang, J.-C. Ding, H.-Y. Wu, J. Braz. Chem. Soc. 19 (2008) 877-883.
[23] S. Hemmati, M.M. Mojtahedi, M.S. Abaee, Z. Vafajoo, S.G. Saremi, M. Noroozi, A. Sedrpoushan, M. Ataee, J. Sulfur Chem. 34 (2013) 347-357.
[24] R. Srinivas, B. Thirupathi, K.P. Kumar, A.N. Prasad, B.M. Reddy, Curr. Org. Chem. 16 (2012) 2482-2489.
[25] B.K. Banik, S. Samajdar, I. Banik, J. Org. Chem. 69 (2004) 213-216.
[26] M. Banik, B. Ramirez, A. Reddy, D. Bandyopadhyay, B.K. Banik, Org. Med. Chem. Lett. 2 (2012) 1-4.
[27] H.S.P. Rao, S. Jothilingam, H.W. Scheeren, Tetrahedron 60 (2004) 1625-1630.
[28] J. Chen, H. Wu, X. Zhang, W. Su, Tetrahedron Lett. 47 (2006) 5383–5387.
[29] M. Curini, F. Montanari, R. Margarita, Tetrahedron Lett. 44 (2003) 3923–3925.
[30] H.R. Darabi, K. Aghapoor, A.D. Farahani, F. Mohsenzadeh, Environ. Chem. Lett. 10 (2012) 369-375.
[31] F.J. Duan, J.C. Ding, H.J. Deng, D.B. Chen, J.X. Chen, M.C. Liu, H.Y. Wu, Chin. Chem. Lett. 24 (2013) 793-796.
[32] Z. Zhang, J. Li, T. Li, Ultrason. Sonochem. 15 (2008) 673-676.
[33] B.F. Mirjalili, A. Bamoniri, Z. Fazeli, Iran. J. Catal. 6 (2016) 253-259.
[34] H.R. Darabi, M.R. Poorheravi, K. Aghapoor, A. Mirzaee, F. Mohsenzadeh, N. Asadollahnejad, H. Taherzadeh, Y. Balavar, Environ. Chem. Lett. 10 (2012) 5-12.
[35] H. Zhao, W. He, Y. Wang, Y. Yue, X. Gao, Z. Li, S. Yan, W. Zhou, X. Zhang, Mater. Chem. Phys. 111 (2008) 265-270.
[36] C.J.F. Souza, E.E. Garcia-Rojas, Food Hydrocolloids 47 (2015) 124-129.
[37] B.K. Banik, S. Samajdar, I. Banik, J. Org. Chem. 69 (2004) 213-216.
[38] H. Lee, B.H. Kim, Tetrahedron 69 (2013) 6698-6708.
[39] W. Bishop, J. Am. Chem. Soc. 67 (1945) 2261-2262.
[40] V. Satyanarayana, A. Sivakumar, Ultrason. Sonochem. 18 (2011) 917-922.