Skip to main content
Log in

The synthesis of sulfonated polyethersulfone (SPES) and the preparation of its membranes as matrix in the immobilization of Candida antarctica lipase B (Cal-B)

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

The immobilization of lipases is often used in biotechnology to improve the performance, reusability, and stability of the enzyme. Candida antarctica lipase B (Cal-B) has been used as a catalyst in trans-esterification reaction. To improve the utilization of Cal-B, therefore the immobilization of Cal-B onto a polymer matrix became crucial. In this study, polyethersulfone (PES) and sulfonated polyethersulfone (SPES) membranes were used as matrices of Cal-B immobilization. SPES was previously synthesized by modifying PES using chlorosulfonic acid (ClSO3H) to improve the immobilization of Cal-B. SPES-PSf (polysulfone) blended membranes were also successfully prepared by blending SPES, PSf, and PEG in N-methylpyrrolidone (NMP) as the solvent using phase-inversion method. The attenuated total reflectance (ATR)–FTIR spectrum showed characteristic peaks of the immobilized Cal-B on the matrix at peak 3184.03 cm−1 (–N–H bonds) and 1683.49 cm−1 (–CH deformation bonds). The Raman spectroscopy of the PES-based membranes before and after sulfonation reaction showed the deviations from the symmetrical structure of PES, with specific Raman shifts at 784.11 cm−1, 1150.95 cm−1, and 1588.9 cm−1. Cal-B was successfully immobilized and loaded onto SPES membrane. By Lowry assay, it was detected that 140.3 μg/cm2 enzyme was successfully loaded into the 17.3 cm2 of membrane. The value was one and a half times higher than PES (91.0 μg/cm2 in 17.3 cm2). However, the hydrolytic activity of Cal-B immobilized onto SPES membrane (17.0 p-NP/min/cm2) was five times lower than Cal-B immobilized onto PES membrane (80.4 p-NP/min/cm2).

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Kucera J (1983) Preparation of starch beads as a support material for enzyme immobilization. Biotechnology 25(2):599–602

    CAS  Google Scholar 

  2. Shuai W, Das RK, Naghdi M, Brar SK (2016) A review on the important aspects of lipase immobilization on nanomaterials. Biotechnol Appl Biochem 64(4):1–39

  3. Gruber CC, Pleiss J (2012) Lipase B from Candida antarctica binds to hydrophobic substrate-water interfaces via hydrophobic anchors surrounding the active site entrance. J Mol Catal B Enzym 84:48–54

    Article  CAS  Google Scholar 

  4. Kulkarni MG, Dalai AK (2006) Waste cooking oil-an economic source for biodiesel: a review. Ind Eng Chem Res 45:2901–2913

    Article  CAS  Google Scholar 

  5. Rodrigues RC, Ortiz C, Berenguer-Murcia Á, Torres R, Fernández-Lafuente R (2013) Modifying enzyme activity and selectivity by immobilization. Chem Soc Rev 42(15):6290–6307

    Article  CAS  Google Scholar 

  6. Iyer PV, Ananthanarayan L (2008) Enzyme stability and stabilization-Aqueous and non-aqueous environment. Process Biochem 43(10):1019–1032

    Article  CAS  Google Scholar 

  7. Sjoholm KH, Cooney M, Minteer SD (2009) Effects of degree of deacetylation on enzyme immobilization in hydrophobically modified chitosan. Carbohydr Polym 77(2):420–424

    Article  CAS  Google Scholar 

  8. Mu L, Zhao W (2009) Applied surface science hydrophilic modification of polyethersulfone porous membranes via a thermal-induced surface crosslinking approach. Appl Surf Sci 255:7273–7278

    Article  CAS  Google Scholar 

  9. Wei Q, Li J, Qian B, Fang B, Zhao C (2009) Preparation, characterization and application of functional polyethersulfone membranes blended with poly(acrylic acid) gels. J Membr Sci 337(1–2):266–273

    Article  CAS  Google Scholar 

  10. Handayani N, Wahyuningrum D, Zulfikar MA, Nurbaiti S, Radiman CL (2016) The synthesis of biodiesel catalyzed by Mucor miehei lipase immobilized onto aminated polyethersulfone membranes. Bioresour Bioprocess 3(1):22

    Article  Google Scholar 

  11. Widhyahrini K, Handayani N, Wahyuningrum D, Nurbaiti S, Radiman CL (2017) The microwave-Assisted synthesis of polyethersulfone (PES) as a matrix in immobilization of Candida antarctica lipase B (Cal-B). Bull Chem React Eng Catal 12(3):343–350

    Article  CAS  Google Scholar 

  12. Hossein Razzaghi M, Safekordi A, Tavakolmoghadam M, Rekabdar F, Hemmati M (2014) Morphological and separation performance study of PVDF/CA blend membranes. J Membr Sci 470:547–557

    Article  CAS  Google Scholar 

  13. Handayani N, Loos K, Wahyuningrum D, Zulfikar MA (2011) Properties of synthesized chlorosulfonated polyethersulfone and polyethersulfone membranes as solid support for lipases immobilization. In: Proceedings of the 2nd international seminar on chemistry 2011, November, pp 21–25

  14. Baek Y, Kang J, Theato P, Yoon J (2012) Measuring hydrophilicity of RO membranes by contact angles via sessile drop and captive bubble method: a comparative study. Desalination 303:23–28

    Article  CAS  Google Scholar 

  15. Cremlyn R (2003) Chlorosulfonic acid: a versatile reagent, vol 56, no 4. Royal Society of Chemistry, Cambridge

  16. Krishnan NN et al (2006) Synthesis and characterization of sulfonated poly(ether sulfone) copolymer membranes for fuel cell applications. J Power Sources 158:1246–1250

    Article  CAS  Google Scholar 

  17. Weisse H, Keul H, Höcker H (2001) A new route to carboxylated poly(ether sulfone)s: synthesis and characterization. Polymer (Guildf) 42(14):5973–5978

    Article  CAS  Google Scholar 

  18. Koenig JL (1971) Raman scattering of synthetic polymers—a review. Appl Spectrosc Rev 4(2):233–305

    Article  CAS  Google Scholar 

  19. Edwards HGM, Brown DR, Dale JA, Plant S (2000) Raman spectroscopy of sulfonated polystyrene resins. Vib Spectrosc 24(2):213–224

    Article  CAS  Google Scholar 

  20. Gillespie RJ, Robinson EA (1962) The Raman spectra of sulphuric, deuterosulphuric, fluorosulphuric, chlorosulphuric, and methanesulphonic acids and their anions. Can J Chem 40(4):644–657

    Article  CAS  Google Scholar 

  21. Handayani N, Loos K, Wahyuningrum D, Zulfikar MA (2012) Immobilization of Mucor miehei lipase onto macroporous aminated polyethersulfone membrane for enzymatic reactions. Membranes (Basel) 2:198–213

    Article  CAS  Google Scholar 

  22. Clark DS, Baileyt JE (1985) A Mathematical model for restricted diffusion effects on macromolecule impregnation in porous supports. Biotechnol Bioeng 27:208–213

    Article  CAS  Google Scholar 

  23. Hebbar RS, Isloor AM, Ismail AF (2017) Contact angle measurements. In: Membrane characterization. Elsevier B.V., pp 219–255

  24. Zisis T, Freddolino PL, Turunen P, Van Teeseling MCF, Rowan AE, Blank KG (2015) Interfacial activation of Candida antarctica Lipase B: combined evidence from experiment and simulation. Biochemistry 54:5969–5979

    Article  CAS  Google Scholar 

  25. Gandhi NN, Patil NS, Sawant SB, Joshi JB, Wangikar PP, Mukesh D (2000) Lipase-catalyzed esterification. Catal Rev 42(4):439–480

    Article  CAS  Google Scholar 

  26. López-Gallego F, Guisán JM, Betancor L (2013) Glutaraldehyde-mediated protein immobilization. In: Guisan JM (ed) Methods in molecular biology, vol 1051, 3rd edn. Humana Press, Totowa, pp 33–41

    Google Scholar 

  27. Chen YZ, Yang CT, Ching CB, Xu R (2008) Immobilization of lipases on hydrophobilized zirconia nanoparticles: highly enantioselective and reusable biocatalysts. Langmuir 24(16):8877–8884

    Article  CAS  Google Scholar 

  28. Ding Z, Liu X, Liu Y, Zhang L (2016) Enhancing the compatibility, hydrophilicity and mechanical properties of polysulfone ultrafiltration membranes with lignocellulose nanofibrils. Polymers (Basel) 8(10):349

    Article  Google Scholar 

  29. Cycler M, Schrag JD (1997) Structure as basis for understanding interfacial properties of lipases. Methods Enzymol 284(1992):3–27

    Article  Google Scholar 

  30. Yunos SM, Harun Z, Basir H (2013) Influence of inorganic additives on the performance of polysulfone ultrafiltration membrane. J. Teknol 65(4):111–115

    Google Scholar 

  31. Rahimpour A, Siavash S, Ghorbani S, Shockravi A (2010) The influence of sulfonated polyethersulfone (SPES) on surface nano-morphology and performance of polyethersulfone (PES) membrane. Appl Surf Sci 256:1825–1831

    Article  CAS  Google Scholar 

  32. Zhao C, Xue J, Ran F, Sun S (2013) Modification of polyethersulfone membranes—a review of methods. Prog Mater Sci 58(1):76–150

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research was funded by Decentralization Research Grant from KEMENRISTEKDIKTI (Ministry of Research, Technology and Higher Education of the Republic of Indonesia) 2015–2016. Our gratitude goes also to Geological Research and Development Center (PPGL) Bandung for SEM analysis. We also thank Dr. Veinardi Suendo for the measurement of Raman spectroscopy in ITB (Institut Teknologi Bandung).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Khusna Widhyahrini.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Widhyahrini, K., Handayani, N., Wahyuningrum, D. et al. The synthesis of sulfonated polyethersulfone (SPES) and the preparation of its membranes as matrix in the immobilization of Candida antarctica lipase B (Cal-B). Polym. Bull. 77, 3735–3748 (2020). https://doi.org/10.1007/s00289-019-02932-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-019-02932-7

Keywords

Navigation