Skip to main content
SpringerLink
Log in

Regenerated coenzyme-based preparation of bienzyme-polymer nanoconjugates and their applications for the synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate

  • Polymer, Industrial Chemistry
  • Published:
Korean Journal of Chemical Engineering Aims and scope Submit manuscript

Abstract

A modular approach was applied for the synthesis of bienzyme-polymer nanoconjugates (nano-BECs) (50–70 nm) consisting of two enzymes (carbonyl reductase and glucose dehydrogenase) conjugated within a single universal polymer scaffold. The amount of the product ethyl (R)-2-hydroxy-4-phenylbutyrate (R-HPBE) with nano-BECs as the catalyst was 533 mM in a dibutyl phthalate-phosphate buffer (dibutyl phthalate-PB) biphasic system, while the amount of R-HPBE was 349 mM using carbonyl reductase-poly(acrylic acid) as the catalyst, indicating that the nano-BECs have an advantage for coenzyme regeneration. Compared with a single aqueous phase, the substrate treatment capacity was improved at the interface of the dibutyl phthalate-PB biphasic system. Under the optimal reaction conditions (35 °C, 40 h, dibutyl phthalate-PB 1: 1), nano-BECs can completely convert substrate into optically pure R-HPBE (enantiomeric excess (e.e.) >99.9%) in the organic-aqueous system.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Z. Q. Zhao, H. L. Wang, Y. P. Zhang, L. F. Chen, K. Wu and D. Z. Wei, Biotechnol. Lett., 38, 1799 (2016).

    Article  CAS  PubMed  Google Scholar 

  2. J. Deng, Z. Q. Yao, K. L. Chen, Y. A. Yuan, J. P. Lina and D. Z. Wei, J. Biotechnol., 217, 31 (2016).

    Article  CAS  PubMed  Google Scholar 

  3. K. Javidnia, E. Faghih-Mirzaei, R. Miri, M. Attarroshan and K. Zomorodian, Indian J. Pharm. Sci., 78, 73 (2016).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. H. L. Zhang C. Zhang, C. H. Pei, M. N. Han and W. Li, J. Appl. Microbiol., 126, 127 (2019).

    Article  CAS  PubMed  Google Scholar 

  5. M. Hibi, K. Takahashi, J. Kako, Y. Wakita, T. Kodera, S. Shimizu, K. Yokozeki and J. Ogawa, Bioorg. Med. Chem., 26, 1327 (2018).

    Article  CAS  PubMed  Google Scholar 

  6. G. C. Xu, Y. P. Zhang, Y. Wang and Y. Ni, Bioresour. Technol., 247, 553 (2018).

    Article  CAS  PubMed  Google Scholar 

  7. Q. Xu, W. Y. Tao, H. Huang and S. Li, Biochem. Eng. J., 106, 61 (2016).

    Article  CAS  Google Scholar 

  8. K. Chen, X. Y. Huang, S. B. J. Kan, R. K. Zhang and F. H. Arnold, Science, 360, 71 (2018).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Y. G. Zheng, H. H. Yin, D. F. Yu, X. Chen, X. L. Tang, X. J. Zhang, Y. P. Xue, Y. J. Wang and Z. Q. Liu, Appl. Microbiol. Biot., 101, 987 (2017).

    Article  CAS  Google Scholar 

  10. S. Oksuz, E. Şahin and E. Dertli, Chem. Biodivers., 15, e1800028 (2018).

    Article  PubMed  Google Scholar 

  11. K. Honda, M. Inoue, T. Ono, K. Okano, Y. Dekishima and H. Kawabata, J. Biosci. Bioeng., 123, 673 (2017).

    Article  CAS  PubMed  Google Scholar 

  12. L. H. Zheng, X. Y. Zhang, Y. P. Bai and J. H. Fan, Algal. Res., 35, 432 (2018).

    Article  Google Scholar 

  13. S. Shah, R. Agera, P. Sharma, A. V. Sunder, H. Bajwa, H. M. James, R. P. Gaikaiwari and P. P. Wangikar, Process Biochem., 70, 71 (2018).

    Article  CAS  Google Scholar 

  14. X. Chen, Z. Q. Liu, C. P. Lin and Y. G. Zheng, Bmc. Biotechnol., 16, 70 (2016).

    Article  PubMed  PubMed Central  Google Scholar 

  15. Z. Q. Liu, L. M. Zhou, P. Liu, P. J. Baker, S. S. Liu, Y. P. Xue, M. Xu and Y. G. Zheng, Appl. Microbiol. Biot., 99, 8891 (2015).

    Article  CAS  Google Scholar 

  16. A. Scomparin, H. F. Florindo, G. Tiram, E. L. Ferhuson and R. Satchi-Fainaro, Adv. Drug Deliv. Rev., 118, 52 (2017).

    Article  CAS  PubMed  Google Scholar 

  17. Z. Y. Sun, U. Glebe, H. Charan, A. Boker and C. Z. Wu, Angew. Chem. Int. Edit., 57, 13810 (2018).

    Article  CAS  Google Scholar 

  18. X. L. Wu, J. Ge, J. Y. Zhu, Y. F. Zhang, Y. Yong and Z. Liu, Chem. Commun., 51, 9674 (2015).

    Article  CAS  Google Scholar 

  19. O. V. Zore, P. Pande, O. Okifo, A. K. Basu, R. M. Kasi and C. V. Kumar, RSC Adv., 7, 29563 (2017).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. X. Huang, M. Li, D. C. Green, D. S. Williams, A. J. Patil and S. Mann, Nat. Commun., 4, 1 (2013).

    Google Scholar 

  21. G. Premaratne, L. Coats and S. Krishnan, Method. Enzymol., 590, 225 (2017).

    Article  CAS  Google Scholar 

  22. P. van Rijn, Polymers, 5, 576 (2013).

    Article  Google Scholar 

  23. N. Suthiwangcharoen and R. Nagarajan, Biomacromolecules, 15, 1142 (2014).

    Article  CAS  PubMed  Google Scholar 

  24. P. Bosiger, G. Tegl, I. M. T. Richard, L. Le Gat, L. Huber, V. Stagl, A. Mensah, G. M. Guebitz, R. M. Rossi and G. Fortunato, Carbohydr. Polym., 181, 551 (2018).

    Article  CAS  PubMed  Google Scholar 

  25. Y. Zhao, Y. Wang, X. B. Zhang, R. M. Kong, L. Xia and F. L. Qu, Talanta, 155, 265 (2016).

    Article  CAS  PubMed  Google Scholar 

  26. S. D. Gur, N. Idil and N. Aksoz, Appl. Biochem. Biotechnol., 184, 538 (2018).

    Article  CAS  PubMed  Google Scholar 

  27. N. S. Rios, C. Mendez-Sanchez, S. Arana-Pea, N. Rueda, C. Ortiz, L. R. B. Goncalves and R. Fernandez-Lafuente, Biochim. Biophys. Acta., 1867, 741 (2019).

    Article  CAS  Google Scholar 

  28. Y. Ido, A. L. B. Macon, M. Iguchi, Y. Ozeki, S. Koeda, A. Obata, T. Kasuga and T. Mizuno, Polymer, 132, 342 (2017).

    Article  CAS  Google Scholar 

  29. D. Skoulas, V. Stuettgen, R. Gaul, S. A. Cryan, D. J. Brayden and A. Heise, Biomacromolecules, 21, 2455 (2020).

    Article  CAS  PubMed  Google Scholar 

  30. C. M. Riccardi, D. Mistri, O. Hart, M. Anuganti, Y. Lin, R. M. Kasi and C. V. Kumar, Chem. Commun., 52, 2593 (2016).

    Article  CAS  Google Scholar 

  31. B. Ozbek and A. Unal, Korean J. Chem. Eng., 34, 1992 (2017).

    Article  CAS  Google Scholar 

  32. V. K. Mudhivarthi, K. S. Cole, M. J. Novak, W. Kipphut, I. K. Deshapriya, Y. X. Zhou, R. M. Kasi and C. V. Kumar, J. Mater. Chem., 22, 20423 (2012).

    Article  CAS  Google Scholar 

  33. R. Chen, J. Deng, J. P. Lin, X. P. Yin, T. Xie, S. L. Yang and D. Z. Wei, Biotechnol. Appl. Bioc., 63, 465 (2016).

    Article  CAS  Google Scholar 

  34. X. L. Qian, J. Pan, N. D. Shen, X. Ju, J. Zhang and J. H. Xu, Biochem. Eng. J., 91, 72 (2014).

    Article  CAS  Google Scholar 

  35. J. Deng, Z. Q. Yao, K. L. Chen, Y. A. Yuan, J. P. Lin and D. Z. Wei, J. Biotechnol., 217, 31 (2016).

    Article  CAS  PubMed  Google Scholar 

  36. Z. G. Wang, S. Zhou, S. L. Zhang, S. Zhang, F. M. Zhu, X. L. Jin, Z. M. Chen and X. L. Xu, Sci. Rep., 7, 4007 (2017).

    Article  PubMed  PubMed Central  Google Scholar 

  37. S. H. Huang and S. W. Tsai, J. Mol. Catal. B: Enzym., 28, 65 (2004).

    Article  CAS  Google Scholar 

  38. P. D’Arrigo, G. Pedrocchi-Fantoni and S. Servi, Tetrahedron: Asymmetry, 21, 914 (2010).

    Article  Google Scholar 

  39. Y. X. Yang, Y. G. Shi, L. F. Feng and S. Y. Tian, Molecules, 25, 2056 (2020).

    Article  CAS  PubMed Central  Google Scholar 

  40. H. A. Klok, J. Polym. Sci. Part A: Polym. Chem., 43, 1 (2005).

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank the National Nature Science Foundation of China (21978267) and the Natural Science Foundation of Zhejiang Province (LY15B060005) for the financial support.

Author information

Authors and Affiliations

  1. College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, Zhejiang, China

    Yuan Lu, Hongqian Dai, Pengpeng Cheng, Lan Tang & Zhimin Ou

  2. The Third Affiliated Hospital of Qiqihar Medical College, Qiqihar, Heilongjiang, China

    Hanbing Shi & Xingyuan Sun

Authors
  1. Yuan Lu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hongqian Dai
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pengpeng Cheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hanbing Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Lan Tang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Xingyuan Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Zhimin Ou
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Xingyuan Sun or Zhimin Ou.

Additional information

Conflict of Interest

The authors declare that they have no competing interests.

Human and Animal Rights Statement

This article does not contain any studies with human participants or animals performed by any of the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lu, Y., Dai, H., Cheng, P. et al. Regenerated coenzyme-based preparation of bienzyme-polymer nanoconjugates and their applications for the synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate. Korean J. Chem. Eng. 38, 1066–1077 (2021). https://doi.org/10.1007/s11814-021-0775-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11814-021-0775-7

Keywords

Search

Navigation