Original enzyme-catalyzed synthesis of chalcones: Utilization of hydrolase promiscuity
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Abstract
An E-chalcone was obtained with very high stereoselectivity for the first time by an enzyme-catalyzed Claisen–Schmidt condensation between benzaldehyde and acetophenone. From a set of lipases, only that from hog pancreas demonstrated promiscuity, catalyzing the reaction in the presence of imidazole as a promoter. Another enzyme, acylase from Aspergillus melleus (EC 3.5.1.14) also proved to be active in the synthesis of E-chalcone under the same reaction conditions. This acylase along with the recombinant D-aminoacylase (EC 3.5.1.81) also catalyzed the reaction between acetophenone and p-nitrobenzaldehyde. Such a "green" approach to the synthesis of chalcones is of great interest because of the important applications of chalcones as formula ingredients in the pharmaceutical, food and cosmetic industries.
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a) S. N. A. Bukhari, X. Zhang, I. Jantan, H. L. Zhu, M. W. Amjad, V. H. Masand, Chem. Biol. Drug Des. 95 (2015) 729; b) I. Jantan, S. N. A. Bukhari, O. A. Adekoya, I. Sylte, Drug Des. Dev. Ther. 8 (2014) 1405; c) S. N. A. Bukhari, Y. Tajuddin, V. J. Benedict, K. W. Lam, I. Jantan, J. Jalil, M. Jasamai, Chem. Biol. Drug Des. 83 (2014) 198; d) K. Sahu, S. S. Balbhadra, J. Choudhary, Curr. Med. Chem. 19 (2012) 209; e) S. N. A. Bukhari, M. Jasamai, I. Jantam, Mini-Rev. Med. Chem. 12 (2012) 1394; f) H. Prashar, A. Chawla, A. K. Sharma, R. Kharb, Int. J. Pharma Sci. Res. 3 (2012) 1913; g) A. M. Katsori, D. Hadji¬pavlou-Litina, Expert Opin. Ther. Pat. 21 (2011) 1575; h) D. Batovska, I. Todorova, Curr. Clin. Pharmacol. 5 (2010) 1; i) D. Batovska, S. Parushev, Int. J. Curr. Chem. 1 (2010) 217; j) J. Mojzis, L. Varinska, G. Mojzisova, I. Kostova, L. Mirossay, Pharmacol. Res. 57 (2008) 259; k) Z. Nowakowska, Eur. J. Med. Chem. 42 (2007) 125; l) L. Ni, C. Meng, J. Sikorski, Expert Opin. Ther. Pat. 14 (2004) 1669; m) J. Dimmock, D. Elias, M. Beazely, N. Kandepu, Curr. Med. Chem. 6 (1999) 1125
a) D. Batovska, S. Parushev, A. Slavova, V. Bankova, I. Tsvetkova, M. Ninova, H. Najdenski, Eur. J. Med. Chem. 42 (2007) 87; b) K. Lahtchev, D. Batovska, S. Parushev, V. Ubiyvovk, A. Sibirny, Eur. J. Med. Chem. 43 (2008) 2220; c) D. Batovska, S. Parushev, B. Stamboliyska, I. Tsvetkova, M. Ninova, H. Najdenski, Eur. J. Med. Chem. 44 (2009) 2211; d) A. Mehandzhiyski, I. Tsvetkova, H. Najdenski, D. Batovska, Bulg. J. Chem. 1 (2012) 53; e) A. Ivanova, D. Batovska, H. Engi, S. Parushev, I. Ocsovszki, I. Kostova, J. Molnar, In vivo 22 (2008) 379; f) A. Ivanova, D. Batovska, I. Todorova, B. Stamboliyska, J. Serly, J. Molnar, Int. J. Med. Chem. 2011 (2011) article ID 530780; g) R. F. Vasilev, V. D. Kancheva, G. F. Fedorova, D. I. Batovska, A. V. Trofimov, Kinet. Catal. 51 (2010) 507; h) D. I. Batovska, G. H. Fedorova, V. D. Kancheva, V. A. Menshov, V. V. Naumov, A. V. Trofimov, Y. B. Tsaplev, R. F. Vasil'ev, T. L. Vep¬rintsev, Luminescence 27 (2012) 99; i) I. Todorova, D. Batovska, B. Stamboliyska, S. Parushev, J. Serb. Chem. Soc. 76 (2011) 491
a) B. Sharma, S. C. Agrawal, K. C. Gupta, Int. J. Chem. Res. 1 (2010) 25; b) A. R. Jagtap, V. S. Satam, R. N. Rajule, V. R. Kanetkar, Dyes Pigm. 91 (2011) 20
Z. Wang, Comprehensive Organic Name Reactions and Reagents. Vol. 3, Wiley-Inter¬science, Hoboken, NJ, 2010, p. 660
a) Q. Xu, Z. Yang, D. Yin, F. Zhang, Catal. Commun. 9 (2008) 1579; b) J. Shen, H. Wang, H. Liu, Y. Sun, Z. Liu, J. Mol. Catal., A: Chem. 280 (2008) 24
a) G. Thirunaratyanan, G. Vanangamudi, Arkivoc 2006(XII) (2006) 58; b) R. K. Saini, N. Kumari, Y. C. Joshi, P. Joshi, S. S. Shekhawat, Asian J. Chem. 19 (2007) 4483
X. Pan, F. Yi, X. Zhang, S. Chen, Asian J. Chem. 24 (2012) 3809
a) E. Perozo-Rondoґn, R. M. Marteґn-Aranda, B. Casal, C. J. Duraґn-Valle, W. N. Lau, X. F. Zhang, K. L. Yeung, Catal. Today 114 (2006) 183; b) J. T. Li, W.-Z. Yang, S.-X. Wang, S.-H. Li, T.-S. Li, Ultrason. Sonochem. 9 (2002) 237
D. Kakati, J. C. Sharma, Chem. Cent. J. 5 (2011) 1
M. M. H. Bhuiyan, M. I. Hossain, M. M. Mahmud, M. Al-Amin, Chem. J. 1 (2011) 21;
b) M. D. Bowman, R. C. Jeske, H. E. Blackwell, Org. Lett. 6 (2004) 2019
a) A. Boumendjel, J. Boccard, P. A. Carrupt, E. Nicolle, M. Blanc, A. Geze, L. Choisnard, D. Wouessidjewe, E. L. Matera, C. Dumontet, J. Med. Chem. 51 (2008) 2307; b) S. Sebti, A. Solhy, R. Tahir, S. Boulaajaj, J. A. Mayoral, J. M. Fraile, A. Kossir, H. Oumimoun, Tetrahedron Lett. 42 (2001) 7953
P. Lozano, T. De Diego, J. L. Iborra, Enzymatic Catalysis. Handbook of Green Chem-istry, Vol. 4, Wiley–VCH, Amsterdam, 2010, p. 281
a) L. Casas-Godoy, S. Duquesne, F. Bordes, G. Sandoval, A. Marty, Methods of Mole¬cular Biology, Vol. 861, Humana Press, New York, 2012, p. 3; b) U. T. Bornscheuer, R. J. Kazlauskas, Hydrolases in Organic Synthesis, 2nd ed., Wiley–VCH, Weinheim, Ger¬many, 2005, p. 61; c) W. Aehle, Enzymes in Industry, 3rd ed., Wiley–VCH, Weinheim, Germany, 2007, p. 108, 171; d) G. Alvaro, A. Illanes, Enzyme Biocatalysis: Principles and Applications, Springer, Amsterdam, 2008, p. 299; e) A. Liese, K. Seelbach, C. Wandrey, Industrial Biotransformations, 2nd ed., Wiley–VCH, Weinheim, 2006, p. 273
a) T. Kitazume, T. Ikeya, K. Murata, J. Chem. Soc., Chem. Commun. 17 (1986) 1331; b) C. Branneby, P. Carlqvist, A. Magnusson, K. Hult, T. Brinck, P. Berglund, J. Am. Chem. Soc. 125 (2003) 874; c) O. Torre, I. Alfonso, V. Gotor, Chem. Commun. 15 (2004) 1724; d) P. Carlqvist, M. Svedendahl, C. Branneby, K. Hult, T. Brinck, P. Berglund, ChemBioChem 6 (2005) 331; e) K. Hult, P. Berglund, Trends Biotechnol. 25 (2007) 231; f) C. Li, X.-W. Feng, N. Wang, Y.-J. Zhou, X.-Q. Yu, Green Chem. 10 (2008) 616.
X. Chen, B.-K. Liu, H. Kang, X.-F. Lin, J. Mol. Catal., B: Enzym. 68 (2011) 71
D. Hwang, J. Hyun, G. Jo, D. Koh, Y. Lim, Magn. Reson. Chem. 49 (2011) 41.