Skip to main content
SpringerLink
Log in

Laccase-catalyzed polymerization of hydroquinone incorporated with chitosan oligosaccharide for enzymatic coloration of cotton

  • Published:
Applied Biochemistry and Biotechnology Aims and scope Submit manuscript

Abstract

Chitosan oligosaccharide (COS), a water-soluble carbohydrate obtained from chemical or enzymatic hydrolysis of chitosan, has similar structure and properties to non-toxic, biocompatible, and biodegradable chitosan. However, COS has many advantages over chitosan due to its low molecular weight and high water solubility. In the current work, COS was incorporated in the laccase-catalyzed polymerization of hydroquinone. The laccase-catalyzed polymerization of hydroquinone with or without COS was investigated by using simple structure of glucosamine hydrochloride as an alternative to COS to understand the mechanism of COS-incorporated polymerization of hydroquinone. Although polyhydroquinone can be regarded as the polymeric colorant with dark brown color, there is no affinity or chemical bonding between polyhydroquinone and cotton fibers. Cotton fabrics were successfully in-situ dyed into brown color through the laccase-catalyzed polymerization of hydroquinone by incorporating with COS as a template. The presence of COS enhanced the dye uptake of polyhydroquinone on cotton fibers due to high affinity of COS to cotton and covalent bonding between COS and polyhydroquinone during laccase catalysis. This novel approach not only provides a simple route for the biological coloration of cotton fabrics but also presents a significant way to prepare functional textiles with antibacterial property.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12

Similar content being viewed by others

References

  1. Sun, T., Zhu, Y., Xie, J., & Yin, X. (2011). Antioxidant activity of N-acyl chitosan oligosaccharide with same substituting degree. Bioorganic & Medicinal Chemistry Letters, 21(2), 798–800.

    Article  CAS  Google Scholar 

  2. Dodane, V., & Vilivalam, V. D. (1998). Pharmaceutical applications of chitosan. Pharmaceutical Science & Technology Today, 1(6), 246–253.

    Article  CAS  Google Scholar 

  3. Zhao, D., Wang, J., Tan, L., Sun, C., & Dong, J. (2013). Synthesis of N-furoyl chitosan and chito-oligosaccharides and evaluation of their antioxidant activity in vitro. International Journal of Biological Macromolecules, 59, 391–395.

    Article  CAS  PubMed  Google Scholar 

  4. Zhou, Y., Yang, H., Liu, X., Mao, J., Gu, S., & Xu, W. (2013). Electrospinning of carboxyethyl chitosan/poly(vinyl alcohol)/silk fibroin nanoparticles for wound dressings. International Journal of Biological Macromolecules, 53(2), 88–92.

    Article  CAS  PubMed  Google Scholar 

  5. Sekiguchi, S., Miura, Y., Kaneko, H., Nishimura, S. I., Nishi, N., Iwase, M., & Tokura, S. (1994). Molecular Weight dependency of antimicrobial activity by chitosan oligomers. In K. Nishinari & E. Doi (Eds.), Food Hydrocolloids (pp. 71–76). Boston: Springer.

    Chapter  Google Scholar 

  6. Du, Y. Z., Wang, L., Yuan, H., Wei, X. H., & Hu, F. Q. (2009). Preparation and characteristics of linoleic acid-grafted chitosan oligosaccharide micelles as a carrier for doxorubicin. Colloids and Surfaces B: Biointerfaces, 69(2), 257–263.

    Article  CAS  PubMed  Google Scholar 

  7. Lin, S. B., Chen, S. H., & Peng, K. C. (2009). Preparation of antibacterial chito-oligosaccharide by altering the degree of deacetylation of β-chitosan in a Trichoderma harzianum chitinase-hydrolysing process. Journal of the Science of Food and Agriculture, 89(2), 238–244.

    Article  CAS  Google Scholar 

  8. Crini, G. (2005). Recent developments in polysaccharide-based materials used as adsorbents in wastewater treatment. Progress in Polymer Science, 30(1), 38–70.

    Article  CAS  Google Scholar 

  9. Berger, J., Reist, M., Mayer, J. M., Felt, O., Peppas, N. A., & Gurny, R. (2004). Structure and interactions in covalently and ionically crosslinked chitosan hydrogels for biomedical applications. European Journal of Pharmaceutics and Biopharmaceutics, 57(1), 19–34.

    Article  CAS  PubMed  Google Scholar 

  10. Je, J. Y., Park, P. J., & Kim, S. K. (2004). Free radical scavenging properties of hetero-chitooligosaccharides using an ESR spectroscopy. Food and Chemical Toxicology, 42(3), 381–387.

    Article  CAS  PubMed  Google Scholar 

  11. Eom, T. K., Senevirathne, M., & Kim, S. K. (2012). Synthesis of phenolic acid conjugated chitooligosaccharides and evaluation of their antioxidant activity. Environmental Toxicology and Pharmacology, 34(2), 519–527.

    Article  CAS  PubMed  Google Scholar 

  12. Tikhonov, V. E., Stepnova, E. A., Babak, V. G., Yamskov, I. A., Palma-Guerrero, J., Jansson, H. B., Lopez-Llorca, L. V., Salinas, J., Gerasimenko, D. V., Avdienko, I. D., & Varlamov, V. P. (2006). Bactericidal and antifungal activities of a low molecular weight chitosan and its N-/2 (3)-(dodec-2-enyl) succinoyl/-derivatives. Carbohydrate Polymers, 64(1), 66–72.

    Article  CAS  Google Scholar 

  13. Toshkova, R., Manolova, N., Gardeva, E., Ignatova, M., Yossifova, L., Rashkov, I., & Alexandrov, M. (2010). Antitumor activity of quaternized chitosan-based electrospun implants against Graffi myeloid tumor. International Journal of Pharmaceutics, 400(1-2), 221–233.

    Article  CAS  PubMed  Google Scholar 

  14. Kim, S. K., & Rajapakse, N. (2005). Enzymatic production and biological activities of chitosan oligosaccharides (COS): a review. Carbohydrate Polymers, 62(4), 357–368.

    Article  CAS  Google Scholar 

  15. Han, J., & Li, X. (2011). Chemoenzymatic syntheses of sialyl Lewis X–chitosan conjugate as potential anti-inflammatory agent. Carbohydrate Polymers, 83(1), 137–143.

    Article  CAS  Google Scholar 

  16. Junker, K., Zandomeneghi, G., Schuler, L. D., Kissner, R., & Walde, P. (2015). Enzymatic polymerization of pyrrole with Trametes versicolor laccase and dioxygen in the presence of vesicles formed from AOT (sodium bis-(2-ethylhexyl) sulfosuccinate) as templates. Synthetic Metals, 200, 123–134.

    Article  CAS  Google Scholar 

  17. Kobayashi, S. (1999). Enzymatic polymerization: a new method of polymer synthesis. Journal of Polymer Science Part A: Polymer Chemistry, 37(16), 3041–3056.

    Article  CAS  Google Scholar 

  18. Kobayashi, S., Uyama, H., & Kimura, S. (2001). Enzymatic polymerization. Chemical Reviews, 101(12), 3793–3818.

    Article  CAS  PubMed  Google Scholar 

  19. Desentis-Mendoza, R. M., Hernández-Sánchez, H., Moreno, A., del C, E. R., Guerrero, L. C., Tamariz, J., & Jaramillo-Flores, M. E. (2006). Enzymatic polymerization of phenolic compounds using laccase and tyrosinase from ustilago m aydis. Biomacromolecules, 7(6), 1845–1854.

    Article  CAS  PubMed  Google Scholar 

  20. Zhang, L., Zhao, W., Ma, Z., Nie, G., & Cui, Y. (2012). Enzymatic polymerization of phenol catalyzed by horseradish peroxidase in aqueous micelle system. European Polymer Journal, 48(3), 580–585.

    Article  CAS  Google Scholar 

  21. Kim, Y. J., Uyama, H., & Kobayashi, S. (2003). Regioselective synthesis of poly (phenylene) as a complex with poly (ethylene glycol) by template polymerization of phenol in water. Macromolecules, 36(14), 5058–5060.

    Article  CAS  Google Scholar 

  22. Kim, Y. J., Uyama, H., & Kobayashi, S. (2004). Peroxidase-catalyzed oxidative polymerization of phenol with a nonionic polymer surfactant template in water. Macromolecular Bioscience, 4(5), 497–502.

    Article  CAS  PubMed  Google Scholar 

  23. Kim, Y. J., Shibata, K., Uyama, H., & Kobayashi, S. (2008). Synthesis of ultrahigh molecular weight phenolic polymers by enzymatic polymerization in the presence of amphiphilic triblock copolymer in water. Polymer, 49(22), 4791–4795.

    Article  CAS  Google Scholar 

  24. Bai, R., Yu, Y., Wang, Q., Fan, X., Wang, P., Yuan, J., & Shen, J. (2018). Laccase-catalyzed poly (ethylene glycol)-templated ‘zip’polymerization of caffeic acid for functionalization of wool fabrics. Journal of Cleaner Production, 191, 48–56.

    Article  CAS  Google Scholar 

  25. Shou, D., Dong, Y., Shen, L., Wu, R., Zhang, Y., Zhang, C., & Zhu, Y. (2013). Rapid quantification of tobramycin and vancomycin by UPLC–TQD and application to osteomyelitis patient samples. Journal of Chromatographic Science, 52(6), 501–507.

    Article  PubMed  CAS  Google Scholar 

  26. Zhou, Q., Cui, L., Ren, L., Wang, P., Deng, C., Wang, Q., & Fan, X. (2018). Preparation of a multifunctional fibroin-based biomaterial via laccase-assisted grafting of chitooligosaccharide. International Journal of Biological Macromolecules, 113, 1062–1072.

    Article  CAS  PubMed  Google Scholar 

  27. Liu, Y., Li, J., Cheng, X., Ren, X., & Huang, T. (2015). Self-assembled antibacterial coating by N-halamine polyelectrolytes on a cellulose substrate. Journal of Materials Chemistry B, 3(7), 1446–1454.

    Article  CAS  PubMed  Google Scholar 

  28. Sakai, S., Yamada, Y., Zenke, T., & Kawakami, K. (2009). Novel chitosan derivative soluble at neutral pH and in-situ gellable via peroxidase-catalyzed enzymatic reaction. Journal of Materials Chemistry, 19(2), 230–235.

    Article  CAS  Google Scholar 

  29. Calafell, M., Díaz, C., Hadzhiyska, H., Gibert, J. M., Dagà, J. M., & Tzanov, T. (2007). Bio-catalyzed coloration of cellulose fibers. Biocatalysis and Biotransformation, 25(2-4), 336–340.

    Article  CAS  Google Scholar 

  30. Sun, X., Bai, R., Zhang, Y., Wang, Q., Fan, X., Yuan, J., & Wang, P. (2013). Laccase-catalyzed oxidative polymerization of phenolic compounds. Applied Biochemistry and Biotechnology, 171(7), 1673–1680.

    Article  CAS  PubMed  Google Scholar 

  31. Liu, H., Liu, X., Yue, L., Jiang, Q., & Xia, W. (2016). Synthesis, characterization and bioactivities of N, O-carbonylated chitosan. International Journal of Biological Macromolecules, 91, 220–226.

    Article  PubMed  CAS  Google Scholar 

  32. Appunni, S., Rajesh, M. P., & Prabhakar, S. (2016). Nitrate decontamination through functionalized chitosan in brackish water. Carbohydrate Polymers, 147, 525–532.

    Article  CAS  PubMed  Google Scholar 

  33. Kamari, A., Aljafree, N. F. A., & Yusoff, S. N. M. (2016). N, N-dimethylhexadecyl carboxymethyl chitosan as a potential carrier agent for rotenone. International Journal of Biological Macromolecules, 88, 263–272.

    Article  CAS  PubMed  Google Scholar 

  34. Muzzarelli, R. A., Tanfani, F., Scarpini, G., & Laterza, G. (1980). The degree of acetylation of chitins by gas chromatography and infrared spectroscopy. Journal of Biochemical and Biophysical Methods, 2(5), 299–306.

    Article  CAS  PubMed  Google Scholar 

  35. Sousa, F., Guebitz, G. M., & Kokol, V. (2009). Antimicrobial and antioxidant properties of chitosan enzymatically functionalized with flavonoids. Process Biochemistry, 44(7), 749–756.

    Article  CAS  Google Scholar 

  36. Božič, M., Gorgieva, S., & Kokol, V. (2012). Homogeneous and heterogeneous methods for laccase-mediated functionalization of chitosan by tannic acid and quercetin. Carbohydrate Polymers, 89(3), 854–864.

    Article  PubMed  CAS  Google Scholar 

  37. Liu, X., Xu, Y., Yu, J., Li, S., Wang, J., Wang, C., & Chu, F. (2014). Integration of lignin and acrylic monomers towards grafted copolymers by free radical polymerization. International Journal of Biological Macromolecules, 67, 483–489.

    Article  CAS  PubMed  Google Scholar 

  38. Mita, N., Tawaki, S. I., Uyama, H., & Kobayashi, S. (2002). Enzymatic oxidative polymerization of phenol in an aqueous solution in the presence of a catalytic amount of cyclodextrin. Macromolecular Bioscience, 2(3), 127–130.

    Article  CAS  Google Scholar 

  39. Li, X., Liu, B. O., Wang, X., Han, Y., Su, H., Zeng, X., & Sun, R. C. (2012). Synthesis, characterization and antioxidant activity of quaternized carboxymethyl chitosan oligosaccharides. Journal of Macromolecular Science, Part A, 49(10), 861–868.

    Article  CAS  Google Scholar 

  40. Rao, V., & Johns, J. (2008). Thermal behavior of chitosan/natural rubber latex blends tg and dsc analysis. Journal of Thermal Analysis and Calorimetry, 92(3), 801–806.

    Article  CAS  Google Scholar 

  41. Kim, S. Y., Zille, A., Murkovic, M., Guebitz, G., & Cavaco-Paulo, A. (2007). Enzymatic polymerization on the surface of functionalized cellulose fibers. Enzyme and Microbial Technology, 40(7), 1782–1787.

    Article  CAS  Google Scholar 

  42. Hadzhiyska, H., Calafell, M., Gibert, J. M., Daga, J. M., & Tzanov, T. (2006). Laccase-assisted dyeing of cotton. Biotechnology Letters, 28(10), 755–759.

    Article  CAS  PubMed  Google Scholar 

  43. Kim, S., Moldes, D., & Cavaco-Paulo, A. (2007). Laccases for enzymatic coloration of unbleached cotton. Enzyme and Microbial Technology, 40(7), 1788–1793.

    Article  CAS  Google Scholar 

  44. Yue, L., Li, J., Chen, W., Liu, X., Jiang, Q., & Xia, W. (2017). Geraniol grafted chitosan oligosaccharide as a potential antibacterial agent. Carbohydrate Polymers, 176, 356–364.

    Article  CAS  PubMed  Google Scholar 

  45. Aytac, Z., Yildiz, Z. I., Kayaci-Senirmak, F., San Keskin, N. O., Tekinay, T., & Uyar, T. (2016). Electrospinning of polymer-free cyclodextrin/geraniol–inclusion complex nanofibers: enhanced shelf-life of geraniol with antibacterial and antioxidant properties. RSC Advances, 6(52), 46089–46099.

    Article  CAS  Google Scholar 

Download references

Funding

This work was financially supported by the National Natural Science Foundation of China (51673087, 31771039), China Scholarship Council (CSC_201706790038), the Program for Changjiang Scholars and Innovative Research Teams in Universities (IRT_15R26), Fundamental Research Funds for the Central Universities (JUSRP51717A), and the Graduate student innovation project (KYLX16_0800).

Author information

Authors and Affiliations

  1. Key Laboratory of Science and Technology of Eco-Textile, Ministry of Education, Jiangnan University, Wuxi, 214122, Jiangsu, China

    Rubing Bai, Yuanyuan Yu, Qiang Wang, Jiugang Yuan & Xuerong Fan

  2. Textile Engineering and Materials Research Group, School of Design, De Montfort University, The Gateway, Leicester, LE1 9BH, UK

    Rubing Bai & Jinsong Shen

Authors
  1. Rubing Bai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yuanyuan Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Qiang Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jinsong Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jiugang Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Xuerong Fan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Qiang Wang.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

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

Bai, R., Yu, Y., Wang, Q. et al. Laccase-catalyzed polymerization of hydroquinone incorporated with chitosan oligosaccharide for enzymatic coloration of cotton. Appl Biochem Biotechnol 191, 605–622 (2020). https://doi.org/10.1007/s12010-019-03169-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12010-019-03169-w

Keywords

Search

Navigation