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Solvent-Free Enzymatic Synthesis of Ethyl 3-Oxobutyrate Derivative: Characterization and Optimization of Reaction Condition

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Abstract

It was first found that porcine pancreatic lipase (PPL) could catalyze the Knoevenagel condensation of aromatic aldehydes and ethyl acetoacetate under solvent-free conditions in this paper. Under solvent-free conditions, the highest yield of PPL catalytic reaction was 99.38%, and the Z/E selectivity of the product was 3.93. In addition, the reaction conditions were optimized, and the factors affecting the product structure were studied.

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References

  1. Vekariya, R. H., & Patel, H. D. (2014). Recent advances in the synthesis of coumarin derivatives via Knoevenagel condensation: A review. Synthetic Commun, 44(19), 2756–2788. https://doi.org/10.1080/00397911.2014.926374

    Article  CAS  Google Scholar 

  2. Appaturi, J. N., Ratti, R., Phoon, B. L., Batagarawa, S. M., Din, I. U., Selvaraj, M., & Ramalingam, R. J. (2021). A review of the recent progress on heterogeneous catalysts for Knoevenagel condensation. Dalton T, 50(13), 4445–4469. https://doi.org/10.1039/d1dt00456e

    Article  CAS  Google Scholar 

  3. He, W.-X., **ng, X., Yang, Z.-J., Yu, Y., Wang, N., & Yu, X.-Q. (2019). Biocatalytic one-pot three-component synthesis of indoloquinolizines with high diastereoselectivity. Catalysis Letters, 249(2), 638–643. https://doi.org/10.1007/s10562-019-02660-7

    Article  CAS  Google Scholar 

  4. Guo X, Xue Z, Xu D, Tu Q, Chang H, Yang X, Huang S (2021) Total synthesis of (–)-brazilane via a lipase-catalyzed desymmetrisation reaction. Nat Prod Res,1–9. https://doi.org/10.1080/14786419.2021.1922403

  5. Sikora, A., Chałupka, J., & Marszałł, M. P. (2020). The use of ion liquids as a Trojan horse strategy in enzyme-catalyzed biotransformation of (R, S)-atenolol. Catalysts, 10(7), 787. https://doi.org/10.3390/catal10070787

    Article  CAS  Google Scholar 

  6. Zhang S, Hyatt J R, Akoh C C (2020) Solvent-free enzymatic synthesis of 1,2-dipalmitoylgall-oylglycerol: Characterization and optimization of reaction condition. Food Chem, 128604. https://doi.org/10.1016/j.foodchem.2020.128604

  7. Feng, X. W., Li, C., Wang, N., Li, K., Zhang, W. W., Wang, Z., & Yu, X. Q. (2009). Lipase-catalysed decarboxylative aldol reaction and decarboxylative Knoevenagel reaction. Green Chemistry, 11, 1933–1936.

    Article  CAS  Google Scholar 

  8. **e, B.-H., Guan, Z., & He, Y.-H. (2012). Biocatalytic Knoevenagel reaction using alkaline protease from Bacillus licheniformis. Biocatal Biotransfor, 30(2), 238–244. https://doi.org/10.3109/10242422.2012.662961

    Article  CAS  Google Scholar 

  9. Hu, W., Guan, Z., Deng, X., & He, Y.-H. (2012). Enzyme catalytic promiscuity: The papain-catalyzed Knoevenagel reaction. Biochimie, 94(3), 656–661. https://doi.org/10.1016/j.biochi.2011.09.018

    Article  CAS  PubMed  Google Scholar 

  10. Wang, Z., Wang, C.-Y., Wang, H.-R., Zhang, H., Su, Y.-L., Ji, T.-F., & Wang, L. (2014). Lipase-catalyzed Knoevenagel condensation between α, β-unsaturated aldehydes and active methylene compounds. Chinese Chemical Letters, 25(5), 802–804. https://doi.org/10.1016/j.cclet.2014.03.036

    Article  CAS  Google Scholar 

  11. Wang, C., Wang, N., Liu, X., Wan, P., He, X., & Shang, Y. (2018). Expanding application of immobilized Candida antarctica lipase B: A green enzyme catalyst for Knoevenagel condensation reaction. Fiber Polym, 19(8), 1611–1617. https://doi.org/10.1007/s12221-018-8200-5

    Article  CAS  Google Scholar 

  12. Lei, Z. G., Chen, B. H., & Koo, Y. M. (2017). Douglas R M (2019) Introduction: Ionic liquids. Chemical Reviews, 117(10), 6633–6635. https://doi.org/10.1021/acs.chemrev.7b00246

    Article  CAS  PubMed  Google Scholar 

  13. El Achkar, T., Greige-Gerges, H., & Fourmentin, S. (2021). Basics and properties of deep eutectic solvents: A review. Environmental Chemistry Letters, 19(4), 3397–3408. https://doi.org/10.1007/s10311-021-01225-8

    Article  CAS  Google Scholar 

  14. Hansen, B. B., Spittle, S., Chen, B., Poe, D., Zhang, Y., Klein, J. M., et al. (2020). Deep eutectic solvents: A review of fundamentals and applications. Chemical Reviews. https://doi.org/10.1021/acs.chemrev.0c00385

    Article  PubMed  Google Scholar 

  15. Gao, G., Wang, P., Liu, P., Zhang, W.-H., Mo, L.-P., & Zhang, Z.-H. (2018). Deep eutectic solvent catalyzed one-pot synthesis of 4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles. Chin J Org Chem, 38, 846–854. https://doi.org/10.6023/cjoc201711014

    Article  CAS  Google Scholar 

  16. Wang, Y., Shang, Z., Wu, T., Fan, J., & Chen, X. (2006). Synthetic and theoretical study on proline-catalyzed Knoevenagel condensation in ionic liquid. Journal of Molecular Catalysis A: Chemical, 253(1–2), 212–221. https://doi.org/10.1016/j.molcata.2006.03.035

    Article  CAS  Google Scholar 

  17. Wang, Y., Cheng, H., He, J.-R., Yao, Q.-X., Li, L.-L., Liang, Z.-H., & Li, X. (2021). Enzymes-catalyzed Knoevenagel condensation promoted by ionic liquid and deep eutectic solvent. Catal Let. https://doi.org/10.1007/s10562-021-03718-1

    Article  Google Scholar 

  18. Abbott, A. P., Boothby, D., Capper, G., Davies, D. L., & Rasheed, R. K. (2004). Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids. Journal of the American Chemical Society, 126(29), 9142–9147. https://doi.org/10.1021/ja048266j

    Article  CAS  PubMed  Google Scholar 

  19. Durand, E., Lecomte, J., & Villeneuve, P. (2013). Deep eutectic solvents: Synthesis, application, and focus on lipase-catalyzed reactions. European Journal of Lipid Science and Technology, 115(4), 379–385. https://doi.org/10.1002/ejlt.201200416

    Article  CAS  Google Scholar 

  20. Y Wang K-H Dong M-L Zhen J-R He Q-X Yao 2024 Experimental and computational study on the factors affecting the structure of L-proline-catalyzed Knoevenagel condensation Biomass ConvBioref 14 11243 11249 https://doi.org/10.1007/s13399-022-03077-w

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Funding

The Natural Science Foundation of Guangdong Province (Grant No.2018A030307022) and Special Innovation Projects of Common Universities in Guangdong Province (Grant No.2018KTSCX126).

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Authors

Contributions

Yun Wang: funding acquisition, project administration, supervision, visualization, writing—original draft, writing—review and editing, conceptualization, methodology. Li-Mao Chen: conceptualization, methodology, writing—original draft, writing—review and editing, validation. **ao-qing Liao: writing—review and editing, formal analysis. Guo-huan Zhang: formal analysis, writing—review and editing. Jie Zhang: writing—review and editing.

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Correspondence to Yun Wang.

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Wang, Y., Chen, LM., Liao, Xq. et al. Solvent-Free Enzymatic Synthesis of Ethyl 3-Oxobutyrate Derivative: Characterization and Optimization of Reaction Condition. Appl Biochem Biotechnol (2024). https://doi.org/10.1007/s12010-024-04981-9

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