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Biosynthesis of Alanyl-Histidine Dipeptide Catalyzed by Papain Immobilized on Magnetic Nanocrystalline Cellulose in Deep Eutectic Solvents

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Abstract

Papain (PA) immobilized onto magnetic nanocrystalline cellulose (PA@MNCC) was successfully fabricated and adopted as an efficient biocatalyst for the synthesis of N-(benzyloxycarbonyl)-alanyl-histidine (Z-Ala-His) dipeptide. Introducing deep eutectic solvents (DESs) as reaction media promoted the synthesis of the Z-Ala-His dipeptide. The effects of reaction conditions on the yield of papain catalytic Z-Ala-His were systematically investigated with the highest yield of 68.4%, which was higher than free papain (63.3%). Besides, this novel PA@MNCC composite can be easily recycled from the reaction system by magnetic forces. In a word, the PA@MNCC composite exhibited great potential for efficient biosynthesis of dipeptide in DESs.

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Abbreviations

PA:

Papain

MNCC:

Magnetic nanocrystalline cellulose

PA@MNCC:

Papain immobilized onto magnetic nanocrystalline cellulose

Z-Ala-His:

N-(Benzyloxycarbonyl)-alanyl-histidine

DESs:

Deep eutectic solvents

Z-Ala-OMe:

N-(Benzyloxycarbonyl)-alanyl methyl ester

TEA:

Triethylamine

References

  1. Chalamaiah, M., Yu, W., & Wu, J. (2018). Immunomodulatory and anticancer protein hydrolysates (peptides) from food proteins: A review. Food Chemistry, 245, 205–222.

    Article  CAS  Google Scholar 

  2. Bhat, Z. F., Kumar, S., & Bhat, H. F. (2015). Bioactive peptides of animal origin: a review. Journal of Food Science and Technology, 52(9), 5377–5392.

    Article  CAS  Google Scholar 

  3. Lange, L., Huang, Y., & Busk, P. K. (2016). Microbial decomposition of keratin in nature-a new hypothesis of industrial relevance. Applied Microbiology and Biotechnology, 100(5), 2083–2096.

    Article  CAS  Google Scholar 

  4. Nissen, P., Hansen, J., Ban, N., Moore, P. B., & Steitz, T. A. (2000). The structural basis of ribosome activity in peptide bond synthesis. Science, 289(5481), 920–930.

    Article  CAS  Google Scholar 

  5. Canabady-Rochelle, L. L. S., Harscoat-Schiavo, C., Kessler, V., Aymes, A., Fournier, F., & Girardet, J. M. (2015). Determination of reducing power and metal chelating ability of antioxidant peptides: revisited methods. Food Chemistry, 183, 129–135.

    Article  CAS  Google Scholar 

  6. Xu, X., You, M., Song, H., Gong, L., & Pan, W. (2018). Investigation of umami and kokumi taste-active components in bovine bone marrow extract produced during enzymatic hydrolysis and Maillard reaction. International Journal of Food Science and Technology, 53(11), 2465–2481.

    Article  CAS  Google Scholar 

  7. Huang, Y., Fang, G., & Liu, L. (2016). Chemical synthesis of proteins using hydrazide intermediates. National Science Review, 3(1), 107–116.

    Article  CAS  Google Scholar 

  8. Bolm, C., & Hernandez, J. G. (2018). From synthesis of amino acids and peptides to enzymatic catalysis: a bottom-up approach in mechanochemistry. ChemSusChem, 11(9), 1410–1420.

    Article  CAS  Google Scholar 

  9. Wang, M., Qi, W., Yu, Q., Su, R., & He, Z. (2011). Kinetically controlled enzymatic synthesis of dipeptide precursor of L-alanyl-L-glutamine. Biotechnology and Applied Biochemistry, 58(6), 449–455.

    Article  CAS  Google Scholar 

  10. Yadav, D. K., Yadav, N., Yadav, S., Haque, S., & Tuteja, N. (2016). An insight into fusion technology aiding efficient recombinant protein production for functional proteomics. Archives of Biochemistry and Biophysics, 612, 57–77.

    Article  CAS  Google Scholar 

  11. Yang, T., Zhao, L., Wang, J., Song, G., Liu, H., Cheng, H., & Yang, Z. (2017). Improving whole-cell biocatalysis by addition of deep eutectic solvents and natural deep eutectic solvents. ACS Sustainable Chemistry & Engineering, 5(7), 5713–5722.

    Article  CAS  Google Scholar 

  12. Sheldon, R. A., & Pereira, P. C. (2017). Biocatalysis engineering: the big picture. Chemical Society Reviews, 46(10), 2678–2691.

    Article  CAS  Google Scholar 

  13. Toledo, M. L., Pereira, M. M., Freire, M. G., Silva, J. P. A., Coutinho, J. A. P., & Tavares, A. P. M. (2019). Laccase activation in deep eutectic solvents. ACS Sustainable Chemistry & Engineering, 7(13), 11806–11814.

    Article  CAS  Google Scholar 

  14. Pätzold, M., Siebenhaller, S., Kara, S., Liese, A., Syldatk, C., & Holtmann, D. (2019). Deep eutectic solvents as efficient solvents in biocatalysis. Trends in Biotechnology, 37(9), 943–959.

    Article  CAS  Google Scholar 

  15. Khandelwal, S., Tailor, Y. K., & Kumar, M. (2016). Deep eutectic solvents (DESs) as eco-friendly and sustainable solvent/catalyst systems in organic transformations. Journal of Molecular Liquids, 215, 345–386.

    Article  CAS  Google Scholar 

  16. Xu, P., Zheng, G., Zong, M., Li, N., & Lou, W. (2017). Recent progress on deep eutectic solvents in biocatalysis. Bioresources and Bioprocessing, 4(1), 34.

    Article  Google Scholar 

  17. Cao, S., Xu, H., Li, X., Lou, W., & Zong, M. (2015). Papain@magnetic nanocrystalline cellulose nanobiocatalyst: a highly efficient biocatalyst for dipeptide biosynthesis in deep eutectic solvents. ACS Sustainable Chemistry & Engineering, 3(7), 1589–1599.

    Article  CAS  Google Scholar 

  18. Li, H., Ni, Y., Cao, X., He, X., Li, G., Chen, K., Ouyang, P., Yang, J., & Tan, W. (2019). Highly active nanobiocatalysis in deep eutectic solvents via metal-driven enzyme-surfactant nanocomposite. Journal of Biotechnology, 292, 39–49.

    Article  CAS  Google Scholar 

  19. Bondeson, D., Mathew, A., & Oksman, K. (2006). Optimization of the isolation of nanocrystals from microcrystalline cellulose by acid hydrolysis. Cellulose, 13(2), 171–180.

    Article  CAS  Google Scholar 

  20. Cao, S., Li, X., Lou, W., & Zong, M. (2014). Preparation of a novel magnetic cellulose nanocrystal and its efficient use for enzyme immobilization. Journal of Materials Chemistry B, 34, 5522.

    Article  CAS  Google Scholar 

  21. Abbott, A. P., Capper, G., Davies, D. L., Rasheed, R. K., & Tambyrajah, V. (2003). Novel solvent properties of choline chloride/urea mixtures. Chemical Communications, 1, 70–71.

    Article  CAS  Google Scholar 

  22. Gates, Z. P., Dhayalan, B., & Kent, S. B. H. (2016). Obviation of hydrogen fluoride in Boc chemistry solid phase peptide synthesis of peptide-(alpha) thioesters. Chemical Communications, 52(97), 13979–13982.

    Article  CAS  Google Scholar 

  23. Shan, Y., Qi, W., Wang, M., Su, R., & He, Z. (2018). Kinetically controlled carboxypeptidase-catalyzed synthesis of novel antioxidant dipeptide precursor BOC-Tyr-Ala. Tianjin University, 24(6), 513–521.

    Article  CAS  Google Scholar 

  24. Kuo, C., Lin, J., Chien, C., Tsai, C., Liu, Y., & Shieh, C. (2016). Formation of amide bond catalyzed by lipase in aqueous phase for peptide synthesis. Journal of Molecular Catalysis B: Enzymatic, 129, 15–20.

    Article  CAS  Google Scholar 

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Funding

This work was supported by the National Natural Science Foundation of China (21908070, 21676104, 21878105), the National Key Research and Development Program of China (2018YFC1603400, 2018YFC1602100), China Postdoctoral Science Foundation (BX20180102, 2019 M652902), and the Fundamental Research Funds for the Central Universities (2019MS100, 2019PY15).

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Authors and Affiliations

  1. Lab of Applied Biocatalysis, School of Food Science and Engineering, South China University of Technology, Guangzhou, 510640, China

    Jun Xiong, Min-Hua Zong, Wen-Yong Lou & Xiao-ling Wu

  2. School of Food Science and Engineering, Foshan University, Foshan, 528000, China

    Shi-Lin Cao

  3. Innovation Center of Bioactive Molecule Development and Application, South China Institute of Collaborative Innovation, Dongguan, 221116, China

    Wen-Yong Lou

Authors
  1. Jun Xiong
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  2. Shi-Lin Cao
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  3. Min-Hua Zong
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  4. Wen-Yong Lou
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  5. Xiao-ling Wu
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Contributions

Jun Xiong, Shi-Lin Cao, Min-Hua Zong, Wen-Yong Lou, and Xiaoling Wu conceived and designed the research; Jun Xiong and Shi-Lin Cao conducted the experiments; Jun Xiong, Shi-Lin Cao, and Xiaoling Wu analyzed and interpreted the data. Jun Xiong and Xiaoling Wu wrote the manuscript. All authors read and approved the manuscript.

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Correspondence to Wen-Yong Lou or Xiao-ling Wu.

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Xiong, J., Cao, SL., Zong, MH. et al. Biosynthesis of Alanyl-Histidine Dipeptide Catalyzed by Papain Immobilized on Magnetic Nanocrystalline Cellulose in Deep Eutectic Solvents. Appl Biochem Biotechnol 192, 573–584 (2020). https://doi.org/10.1007/s12010-020-03345-3

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