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Enzyme-catalyzed synthesis of bioactive heterocycles

  • Gyan Chandra Pariyar and Pranab Ghosh EMAIL logo
Published/Copyright: December 16, 2021
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Abstract

Enzymes are proteins that functions as biological catalyst. It is now a known fact that enzyme can catalyze many synthetic operations better than the conventional reagents. Not only in the synthesis of natural products, they can also be applied for construction of varieties of unnatural compounds. In this chapter, Pariyar and Ghosh have discussed in brief synthesis of various biologically active heterocyclic compounds using different enzymes as catalysts. Among various enzymes, laccases, trypsin, α-amylase and Bakers’ yeast are few that are easily available and have been extensively explored for various synthetic strategies. This chapter will definitely serve as valuable source of information to the readers in the field of enzyme-catalyzed reactions.


Corresponding author: Pranab Ghosh, Department of Chemistry, University of North Bengal, Dist. Darjeeling, West Bengal, India, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Wong, C-H. Enzymatic catalysts in organic synthesis. Science 1989;244:1145–52. https://doi.org/10.1126/science.2658059.Search in Google Scholar

2. Jones, JB. Tetrahedron report number 203: enzymes in organic synthesis. Tetrahedron 1986;42:3351–403. https://doi.org/10.1016/s0040-4020(01)87306-3.Search in Google Scholar

3. Toone, EJ, Simon, ES, Bednarski, MD, Whitesides, GM. Enzyme-catalyzed synthesis of carbohydrates. Tetrahedron 1989;45:5365–422. https://doi.org/10.1016/s0040-4020(01)89487-4.Search in Google Scholar

4. Tramontano, A, Janda, KD, Lemer, RA. Catalytic antibodies. Science 1986;234:1566–70. https://doi.org/10.1126/science.3787261.Search in Google Scholar PubMed

5. Pollack, SJ, Jacobs, JW, Schultz, PG. Selective chemical catalysis by an antibody. Science 1986;234:1570–3. https://doi.org/10.1126/science.3787262.Search in Google Scholar PubMed

6. Hilvert, D, Nared, KD. Stereospecific claisen rearrangement catalyzed by an antibody. J Am Chem Soc 1988;110:5593–4. https://doi.org/10.1021/ja00224a066.Search in Google Scholar

7. Nicolaou, KC, Pfefferkorn, JA, Roecker, AJ, Cao, GQ, Barluenga, S, Mitchell, HJ. Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans. J Am Chem Soc 2000;122:9939–53. https://doi.org/10.1021/ja002033k.Search in Google Scholar

8. Lerner, RA, Benkovic, SJ. Observations in the interface between immunology and chemistry. Chemtracts Org Chem 1990;3:1–36.10.1002/chin.199029325Search in Google Scholar

9. Lu, D, Li, Y, Gong, YJ. Organocatalytic asymmetric tandem Michael addition−hemiacetalization: a route to chiral dihydrocoumarins, chromanes, and 4H-chromenes. J Org Chem 2010;75:6900–7. https://doi.org/10.1021/jo101446d.Search in Google Scholar PubMed

10. Stachulski, AV, Berry, NG, Low, ACL, Moores, SL, Row, E, Warhurst, DC, et al.. Identification of isoflavone derivatives as effective anticryptosporidial agents in vitro and in vivo. J Med Chem 2006;49:1450–4. https://doi.org/10.1021/jm050973f.Search in Google Scholar PubMed

11. Elinson, MN, Dorofeev, AS, Miloserdov, FM, Ilovaisky, AI, Feducovich, SK, Belyakov, PA, et al.. Catalysis of salicylaldehydes and two different C–H acids with electricity: first example of an efficient multicomponent approach to the design of functionalized medicinally privileged 2-amino-4H-chromene scaffold. Adv Synth Catal 2008;350:591–601. https://doi.org/10.1002/adsc.200700493.Search in Google Scholar

12. Sun, W, Cama, LJ, Birzin, ET, Warrier, S, Locco, L, Mosley, R, et al.. 6H-Benzo[c]chromen-6-one derivatives as selective ERbeta agonists. Bioorg Med Chem Lett 2006;16:1468–72. https://doi.org/10.1016/j.bmcl.2005.12.057.Search in Google Scholar PubMed

13. Mitra, B, Pariyar, GC, Ghosh, P. β-Cyclodextrin: a supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one. RSC Adv 2021;11:1271–81. https://doi.org/10.1039/d0ra09562a.Search in Google Scholar PubMed PubMed Central

14. Dey, S, Basak, P, Ghosh, P. A green synthetic approach towards one pot multi component synthesis of hexahydroquinoline and 9-arylhexahydroacridine-1,8-dione derivatives catalyzed by sulphonated rice husk. ChemistrySelect 2020;5:15209–17. https://doi.org/10.1002/slct.202004121.Search in Google Scholar

15. Pariyar, GC, Mitra, B, Mukherjee, S, Ghosh, P. Ascorbic acid as an efficient organocatalyst for the synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-one and 2-substituted quinazolin-4(3H)-one in water. ChemistrySelect 2020;5:104–8. https://doi.org/10.1002/slct.201903937.Search in Google Scholar

16. Singha, R, Basak, P, Bhattacharya, M, Ghosh, P. Graphene oxide catalyzed one-pot synthesis of pyrimido[4,5-b]quinolinone-2,4-diones and their biological evaluation. ChemistrySelect 2020;5:6514–25. https://doi.org/10.1002/slct.202000989.Search in Google Scholar

17. Choudhury, P, Ghosh, P, Basu, B. Amine-functionalized graphene oxide nanosheets (AFGONs): an efficient bifunctional catalyst for selective formation of 1,4-dihydropyridines, acridinediones and polyhydroquinolines. Mol Divers 2020;24:283–94. https://doi.org/10.1007/s11030-019-09949-0.Search in Google Scholar PubMed

18. Mitra, B, Pariyar, GC, Ghosh, P. Glycerol: a benign solvent-assisted metal-free one-pot multi-component synthesis of 4H-thiopyran and thioamides from easily accessible precursors. ChemistrySelect 2019;4:5476–83. https://doi.org/10.1002/slct.201900982.Search in Google Scholar

19. Saha, B, Mitra, B, Brahmin, D, Sinha, B, Ghosh, P. 2-Iodo benzoic acid: an unconventional precursor for the one pot multi-component synthesis of quinoxaline using organo Cu (II) catalyst. Tetrahedron Lett 2018;59:3657–63. https://doi.org/10.1016/j.tetlet.2018.08.051.Search in Google Scholar

20. Bhattacharya, S, Ghosh, P, Basu, B. Graphene oxide (GO): an efficient carbocatalyst for the benign synthesis of functionalized 1,4-benzothiazines. Tetrahedron Lett 2017;58:926–31. https://doi.org/10.1016/j.tetlet.2017.01.068.Search in Google Scholar

21. Xue, Y, Li, L-P, He, Y-H, Guan, Z. Protease-catalysed direct asymmetric Mannich reaction in organic solvent. Sci Rep 2012;2:761–4. https://doi.org/10.1038/srep00761.Search in Google Scholar PubMed PubMed Central

22. Zhang, W, Chen, P, Zhao, Z, Wang, L, Wang, S, Tang, T, et al.. Catalyzed by lipase immobilized on magnetic nanoparticles. Green Chem Lett Rev 2018;11:246–53. https://doi.org/10.1080/17518253.2018.1474271.Search in Google Scholar

23. Zhang, W, Zhao, Z, Wang, Z, Guo, C, Wang, C, Zhao, R, et al.. Lipase-catalyzed synthesis of indolyl 4H-chromenes via a multicomponent reaction in ionic liquid. Catalysts 2017;7:185–94. https://doi.org/10.3390/catal7060185.Search in Google Scholar

24. Wang, L, Li, C, Wang, N, Li, K, Chen, X, Yu, X-Q. Enzyme-mediated domino synthesis of 2-alkylbenzimidazoles in solvent-free system: a green route to heterocyclic compound. J Mol Catal B Enzym 2010;67:16–20. https://doi.org/10.1016/j.molcatb.2010.06.013.Search in Google Scholar

25. Mona, HS. Titania (TiO2)-catalyzed expedient, solventless and mild synthesis of bis(indolyl)methanes. Acta Chim Slov 2007;54:354–9.Search in Google Scholar

26. Pradhan, PK, Dey, S, Giri, VS, Jaisankar, P. InCl3-HMTA as a methylene donor: one-pot synthesis of diindolylmethane (DIM) and its derivatives. Synthesis 2005;11:1779–82.10.1002/chin.200547117Search in Google Scholar

27. Xiang, Z, Liu, Z, Chen, X, Wu, Q, Lin, XF. Biocatalysts for cascade reaction: porcine pancreas lipase (PPL)-catalyzed synthesis of bis(indolyl)alkanes. Amino Acids 2013;45:937–45. https://doi.org/10.1007/s00726-013-1547-4.Search in Google Scholar PubMed

28. Xu, J-C, Li, W-M, Zheng, H, Lai, Y-F, Zhang, P-F. One-pot synthesis of tetrahydrochromene derivatives catalyzed by lipase. Tetrahedron 2011;67:9582–7. https://doi.org/10.1016/j.tet.2011.09.137.Search in Google Scholar

29. Yang, F, Wang, H, Jiang, L, Yue, H, Zhang, H, Wang, Z, et al.. A green and one-pot synthesis of benzo[g]chromene derivatives through a multi-component reaction catalyzed by lipase. RSC Adv 2015;5:5213–6. https://doi.org/10.1039/c4ra13272f.Search in Google Scholar

30. Zhang, Y, Zhang, Y, Ren, Y, Ramström, O. Synthesis of chiral oxazolidinone derivatives through lipase-catalyzed kinetic resolution. J Mol Catal B Enzym 2015;122:29–34. https://doi.org/10.1016/j.molcatb.2015.08.004.Search in Google Scholar

31. Yadav, GD, Pawar, SV. Novelty of immobilized enzymatic synthesis of 3-ethyl-1,3-oxazolidin-2-one using 2-aminoalcohol and dimethylcarbonate: mechanism and kinetic modeling of consecutive reactions. J Mol Catal B Enzym 2014;109:62–9. https://doi.org/10.1016/j.molcatb.2014.08.001.Search in Google Scholar

32. Zhang, M-J, Li, R, He, Y-H, Guan, Z. Pepsin-catalyzed vinylogous Michael addition of deconjugated butenolides and maleimides in water. Catal Commun 2017;98:85–9. https://doi.org/10.1016/j.catcom.2017.03.021.Search in Google Scholar

33. Zheng, H, Shi, Q, Du, K, Mei, Y, Zhang, P. A novel enzyme-catalyzed synthesis of N substituted pyrrole derivatives. Mol Divers 2013;17:245–50. https://doi.org/10.1007/s11030-013-9426-1.Search in Google Scholar PubMed

34. Dutt, S, Goel, V, Garg, N, Choudhury, D, Mallick, D, Tyagi, V. Biocatalytic aza-Michael addition of aromatic amines to enone using α-amylase in water. Adv Synth Catal 2020;362:858–66. https://doi.org/10.1002/adsc.201901254.Search in Google Scholar

35. Pratap, UR, Mali, JR, Jawale, DV, Mane, RA. Bakers’ yeast catalyzed synthesis of benzothiazoles in an organic medium. Tetrahedron Lett 2009;50:1352–4. https://doi.org/10.1016/j.tetlet.2009.01.032.Search in Google Scholar

36. Liu, Z-Q, Xiang, Z-W, Wu, Q, Lin, X-F. Unexpected three-component domino synthesis of pyridin-2-ones catalyzed by promiscuous acylase in non-aqueous solvent. Biochimie 2013;95:1462–5. https://doi.org/10.1016/j.biochi.2013.03.012.Search in Google Scholar PubMed

37. Yu, Y, Zhang, W, Gong, Q-T, Liu, Y-H, Yang, Z-J, He, W-X, et al.. Enzyme-catalysed one-pot synthesis of 4H-pyrimido[2,1-b] benzothiazoles and their application in subcellular imaging. J Biotechnol 2020;324:91–8. https://doi.org/10.1016/j.jbiotec.2020.09.014.Search in Google Scholar PubMed

38. Rahimi, A, Habibi, D, Rostami, A, Zolfigol, MA, Mallakpour, S. Laccase-catalyzed, aerobic oxidative coupling of 4-substituted urazoles with sodium arylsulfinates: green and mild procedure for the synthesis of arylsulfonyl triazolidinediones. Tetrahedron Lett 2018;59:383–7. https://doi.org/10.1016/j.tetlet.2017.12.048.Search in Google Scholar

39. Cannatelli, MD, Ragauskas, AJ. Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones. J Mol Catal B Enzym 2015;119:85–9. https://doi.org/10.1016/j.molcatb.2015.05.016.Search in Google Scholar

40. Hahn, V, Davids, T, Lalk, M, Schauer, F, Mikolasch, A. Enzymatic cyclizations using laccases: multiple bond formation between dihydroxybenzoic acid derivatives and aromatic amines. Green Chem 2010;12:879–87. https://doi.org/10.1039/b920081a.Search in Google Scholar

41. Abdel-Mohsen, H, Conrad, J, Beifuss, U. Laccase-catalyzed oxidation of Hantzsch 1,4-dihydropyridines to pyridines and a new one pot synthesis of pyridines. Green Chem 2012;14:2686–90. https://doi.org/10.1039/c2gc35950b.Search in Google Scholar

42. Hajdok, S, Leutbecher, H, Greiner, G, Conrad, J, Beifuss, U. Laccase initiated oxidative domino reactions for the efficient synthesis of 3,4-dihydro-7,8-dihydroxy-2H-dibenzofuran-1-ones. Tetrahedron Lett 2007;48:5073–6. https://doi.org/10.1016/j.tetlet.2007.05.089.Search in Google Scholar

43. Hajdok, S, Conrad, J, Leutbecher, H, Strobel, S, Schleid, T, Beifuss, U. The laccase-catalyzed domino reaction between catechols and heterocyclic 1,3-dicarbonyls and the unambiguous structure elucidation of the products by NMR spectroscopy and X-ray crystal structure analysis. J Org Chem 2009;74:7230–7. https://doi.org/10.1021/jo9011915.Search in Google Scholar PubMed

44. Ganachaud, C, Garfagnoli, V, Tron, T, Iacazio, G. Trimerisation of indole through laccase catalysis. Tetrahedron Lett 2008;49:2476–8. https://doi.org/10.1016/j.tetlet.2008.02.021.Search in Google Scholar

45. Leutbecher, H, Constantin, M-A, Mika, S, Conrad, J, Beifuss, U. A new laccase-catalyzed domino process and its application to the efficient synthesis of 2-aryl-1H-benzimidazoles. Tetrahedron Lett 2011;52:604–7. https://doi.org/10.1016/j.tetlet.2010.11.145.Search in Google Scholar

46. Maphupha, M, Juma, WP, de Koning, CB, Brady, D. A modern and practical laccase-catalysed route suitable for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles. RSC Adv 2018;8:39496–510. https://doi.org/10.1039/c8ra07377e.Search in Google Scholar PubMed PubMed Central

47. Cannatellia, MD, Ragauskas, AJ. Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – a comparative study. Tetrahedron Lett 2016;57:3749–53. https://doi.org/10.1016/j.tetlet.2016.07.016.Search in Google Scholar

48. Abdel-Mohsen, HT, Conrad, J, Beifuss, U. Laccase-catalyzed domino reaction between catechols and 6-substituted 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles for the synthesis of pyrimidobenzothiazole derivatives. J Org Chem 2013;78:7986–8003. https://doi.org/10.1021/jo401193e.Search in Google Scholar PubMed

49. Liu, L-S, Xie, Z-B, Zhang, C, Fu, L-H, Zhu, H-B, Le, Z-G. α-Chymotrypsin-catalyzed synthesis of 2-substituted benzimidazole through retro-Claisen reaction. Green Chem Lett Rev 2018;11:503–7. https://doi.org/10.1080/17518253.2018.1540726.Search in Google Scholar

50. Ling, J, Wenting, YE, Weike, SU, Chuanming, YU. Application of enzymatic promiscuity in pharmaceutical synthesis: papain-catalyzed one-pot synthesis of 1,4-dihydropyridine calcium channel antagonists and derivatives. Chem Res Chin Univ 2019;35:21–5.10.1007/s40242-019-8273-8Search in Google Scholar

Published Online: 2021-12-16

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