Skip to main content
Log in

Production of d-allose from d-fructose using immobilized l-rhamnose isomerase and d-psicose 3-epimerase

  • Research Paper
  • Published:
Bioprocess and Biosystems Engineering Aims and scope Submit manuscript

Abstract

d-Allose is a rare sugar, can be used as an ingredient in a range of foods and dietary supplements, has alimentary activities, especially excellent anti-cancer effects and used in assisting cancer chemotherapy and radiotherapy, etc. To develop a simple and low-cost process for d-allose production, a one-pot enzymatic process using the substrate of d-fructose, and the recombinant enzymes of d-psicose 3-epimerase (DPE) and l-rhamnose isomerase (l-RhI) was developed. These enzymes were cloned from Ruminococcus sp. and B. subtilis, respectively, successfully expressed in E. coli, extracted and immobilized using anion exchange resin and amino resin, respectively. The mass ratio of d-fructose, d-psicose and d-allose was 6.6:2.4:1.0 when the reaction reached equilibrium after 5 h of reaction. Using the low-cost substrate of d-fructose, the reusable immobilized enzymes and the one-pot reaction, the production process is simplified and the production cost is decreased. In addition, to simplify the enzyme extraction and immobilization processes, new methods for enzyme capture and immobilization were developed especially for DPE immobilization. This is the first report for one-pot d-allose production using immobilized l-RhI and DPE.

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

Access this article

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Explore related subjects

Discover the latest articles and news from researchers in related subjects, suggested using machine learning.

References

  1. Hirooka K, Miyamoto O, Jinming P (2006) Neuroprotective effects of d-allose against retinal ischemia-reperfusion injury. Invest Ophthalmol Vis Sci 47:1653–1657

    Article  Google Scholar 

  2. Hossain MA, Izuishi K, Tokuda M (2004) d-Allose has a strong suppressive effect against ischemia/reperfusion injury: a comparative study with allopurinol and superoxide dismutase. J Hepato-Biliary-Pan 11:181–189

    Google Scholar 

  3. Hossain MA, Wakabayashi H, Goda F (2000) Effect of the immunosuppressants FK506 and d-allose on allogenic orthotopic liver transplantation in rats. Transpl P 32: 2021–2023.

    Article  CAS  Google Scholar 

  4. Hossain MA, Wakabayashi H, Izuishi K (2006) Improved microcirculatory effect of d-allose on hepatic ischemia reperfusion following partial hepatectomy in cirrhotic rat liver. J Biosci Bioeng 101:369–371

    Article  CAS  Google Scholar 

  5. Sui L, Dong Y, Watanabe Y (2005) The inhibitory effect and possible mechanisms of d-allose on cancer cell proliferation. Int J Oncol 27:907–912

    CAS  PubMed  Google Scholar 

  6. Yamaguchi F, Takata M, Kamitori K (2008) Rare sugar d-allose induces specific up-regulation of TXNIP and subsequent G1 cell cycle arrest in hepatocellular carcinoma cells by stabilization of p27kip1. Int J Oncol 32:377–385

    CAS  PubMed  Google Scholar 

  7. Seo MJ, Choi JH, Kang SH (2017) Characterization of l-rhamnose isomerase from Clostridium stercorarium and its application to the production of d-allose from d-allulose (d-psicose). Biotechnol Lett 40:325–334

    Article  Google Scholar 

  8. Roos AK, Mariano S, Kowalinski E (2008) d-ribose-5-phosphate isomerase B from Escherichia coli is also a functional d-allose-6-phosphate isomerase, while the Mycobacterium tuberculosis enzyme is not. J Mol Biol 382:667–679

    Article  CAS  Google Scholar 

  9. Park HY, Park CS, Kim HJ, Oh DK (2007) Substrate specificity of a galactose 6-phosphate isomerase from Lactococcus lactis that produces d-allose from d-psicose. J Biotechnol 132:88–95

    Article  CAS  Google Scholar 

  10. Menavuvu BT, Poonperm W, Leang K (2006) Efficient biosynthesis of d-allose from d-psicose by cross-linked recombinant l-rhamnose isomerase: separation of product by ethanol crystallization. J Biosci Bioeng 101:340

    Article  CAS  Google Scholar 

  11. Feng Z, Mu W, Jiang B (2013) Characterization of ribose-5-phosphate isomerase converting d-psicose to d-allose from Thermotoga lettingae TMO. Biotechnol Lett 35:719–724

    Article  CAS  Google Scholar 

  12. Li C, Lin J, Guo Q (2017) d-Psicose 3-epimerase secretory overexpression, immobilization, and d-psicose biotransformation, separation and crystallization. J Chem Technol Biot 93:350–357

    Article  Google Scholar 

  13. Chul SP, Taeyong K, Hong SH (2016) d-allulose production from d-fructose by permeabilized recombinant cells of Corynebacterium glutamicum cells expressing d-allulose 3-epimerase Flavonifractor plautii. PLoS ONE 11:e0160044

    Article  Google Scholar 

  14. Bai W, Zhu Y, Men Y (2012) Bioconversion of d-fructose to d-allose by novel isomerases. Chin J Biotechnol 28(4):457–459

    CAS  Google Scholar 

  15. Subramanian A, Woodward J (1999) Comparison of techniques for enzyme immobilization on silicon supports. Enzyme Microbial Technol 24(1):26–34

    Article  CAS  Google Scholar 

  16. Yunus IS, Tsai SL (2015) Designed biomolecule-cellulose complexes for rapid palladium recovery and detoxification. RSC Adv 5:20276–20282

    Article  CAS  Google Scholar 

  17. Gade VK, Shirale DJ (2006) Immobilization of GOD on electrochemically synthesized Ppy–PVS composite film by cross-linking via glutaraldehyde for determination of glucose. React Funct Polym 66(12):1420–1426

    Article  CAS  Google Scholar 

  18. Li C, Lin J, Gao L (2018) Modeling and simulation of enzymatic gluconic acid production using immobilized enzyme and CSTR-PFTR circulation reaction system. Biotechnol Lett 40:649–657

    Article  CAS  Google Scholar 

  19. Li C, Zhang C, Lin J (2018) Enzymatic fructose removal from d-psicose bioproduction model solution and the system modeling and simulation. J Chem Technol Biot 93:1249–1260

    Article  CAS  Google Scholar 

  20. Zhu Y, Men Y, Bai W (2012) Overexpression of d-psicose 3-epimerase from Ruminococcus sp. in Escherichia coli and its potential application in d-psicose production. Biotechnol Lett 34:1901–1906

    Article  Google Scholar 

  21. Fox JD, Kapust RB, Waugh DS (2001) Single amino acid substitutions on the surface of Escherichia coli maltose-binding protein can have a profound impact on the solubility of fusion proteins. Protein Sci 10:622–630

    Article  CAS  Google Scholar 

  22. Liu N, Fu M, Wang Y (2012) Immobilization of Lecitase® Ultra onto a novel polystyrene DA-201 resin: characterization and biochemical properties. Appl Biochem Biotech 168:1108–1120

    Article  CAS  Google Scholar 

  23. Bai W, Shen J, Zhu Y (2015) Characteristics and kinetic properties of l-rhamnose isomerase from Bacillus Subtilis by isothermal titration calorimetry for the production of d-Allose. Food Sci Technol Res 21:13–22

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research was funded by the Key R & D Plan of Shandong Province in 2019 (2019GSF107015), and Shandong Province Science and Technology Development Project (2015GSF121016) of China.

Author information

Authors and Affiliations

Contributions

CL and JL designed this study; CL and JL conducted the experiments; CL, LG, KD, HL, JL, and JL analyzed the data; CL and JL wrote the paper; YR revised the manuscript. All the authors have read the manuscript critically.

Corresponding authors

Correspondence to Jianqun Lin or Jianqiang Lin.

Ethics declarations

Conflict of interest

All the authors declare that there is no conflict of interest.

Ethical statement

The authors declare that there are no studies conducted with human participants or animals.

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

Li, C., Gao, L., Du, K. et al. Production of d-allose from d-fructose using immobilized l-rhamnose isomerase and d-psicose 3-epimerase. Bioprocess Biosyst Eng 43, 645–653 (2020). https://doi.org/10.1007/s00449-019-02262-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00449-019-02262-y

Keywords