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Biosynthesis of sucrose-6-acetate catalyzed by surfactant-coated Candida rugosa lipase immobilized on sol–gel supports

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Abstract

Sucrose-6-acetate is an important intermediate in the preparation of sucralose (a finest sweetener). In our study, Candida rugosa lipase coated with surfactant was firstly immobilized on sol–gel supports. Then, the immobilized enzyme was used in the regioselective synthesis of sucrose-6-acetate by transesterification of sucrose and vinyl acetate. The screening results revealed that Tween 80 was an ideal surfactant to coat lipase immobilized in sol–gel and exhibited the highest yield of sucrose-6-acetate. Other factors that influenced the yield during the preparation process were also studied. Under optimal conditions, the yield of sucrose-6-acetate could reach up to 78.68 %, while free lipase was easily inactivated in polar solvent. Thermal and operational stabilities were also improved significantly. Surfactant-coated lipase immobilized in sol–gel remained stable when the temperature was higher than 60 °C. Moreover, they could maintain high catalytic activity after six recycles. This strategy is economical, convenient and promising for the food industry.

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References

  1. Ferrer M, Soliveri J, Plou FJ (2005) Synthesis of sugar esters in solvent mixtures by lipase from Thermomyces lanuginosus and Candida Antarctica B, and their antimicrobial properties. Enzym Microb Technol 36:391–398

    Article  CAS  Google Scholar 

  2. Hill K, Rhode O (1999) Sugar-based surfactants for consumer products and technical applications. Eur J Lipid Sci Technol 101:25–33

    CAS  Google Scholar 

  3. Vlahov IR, Vlahova PI, Linhardt RJ (1997) Regioselective synthesis of sucrose monoesters as surfactants. J Carbohydr Chem 16:1–10

    Article  CAS  Google Scholar 

  4. Han YW, Liu GM, Huang DY, Qiao BJ, Chen LP, Guan LH, Mao DB (2011) Study on the synthesis of sucrose-6-acetate catalyzed by fructosyltransferase from Aspergillus oryzae. New Biotechnol 28:14–18

    Article  CAS  Google Scholar 

  5. Sabeder S, Habulin M, Knez Z (2006) Lipase-catalyzed synthesis of fatty acid fructose esters. J Food Eng 77:880–886

    Article  CAS  Google Scholar 

  6. Ha SH, Hiep NM, Lee SH, Koo YM (2010) Optimization of lipase-catalyzed glucose ester synthesis in ionic liquids. Bioprocess Biosyst Eng 33:63–70

    Article  CAS  Google Scholar 

  7. Zhao X, Wei D, Song Q, Zhang M (2007) Study of ibuprofen glucopyranoside derivative synthesis by Candida Antarctica lipase in organic solvent. Prep Biochem Biotechnol 37:27–34

    Article  CAS  Google Scholar 

  8. Shi YG, Li JR, Chu YH (2011) Enzyme-catalyzed regioselective synthesis of sucrose-based esters. J Chem Technol Biotechnol 86:1457–1468

    Article  CAS  Google Scholar 

  9. Li GY, Cai YJ, Hao ZK, Liao XR (2011) Synthesis of sucrose acetate using a solvent-stable serine protease from Serratia sp. SYBC H Eng Life Sci 11:615–619

    Article  CAS  Google Scholar 

  10. Kennedy JF, Kumar H, Panesar PS, Marwaha SS, Goyal R, Parmar A, Kaur S (2006) Enzyme-catalyzed regioselective synthesis of sugar esters and related compounds. J Chem Technol Biotechnol 81:866–876

    Article  CAS  Google Scholar 

  11. Ferrer M, Cruces MA, Bernabe M, Ballesteros A, Plou FJ (1999) Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures. Biotechnol Bioeng 65:10–16

    Article  CAS  Google Scholar 

  12. Ritthitham S, Wimmer R, Pedersen LH (2011) Polar co-solvents in tertiary alcohols effect initial reaction rates and regio-isomeric ratio ranging from 1.2 to 2.2 in a lipase catalysed synthesis of 6-O- and 6′-O-stearoyl sucrose. Process Biochem 46:931–935

    Article  CAS  Google Scholar 

  13. Weber HK, Stecher H, Faber K (1995) Sensitivity of microbial lipases to acetaldehyde formed by acyl-transfer reactions from vinyl esters. Biotechnol Lett 17:803–808

    Article  CAS  Google Scholar 

  14. Berger B, Faber K (1991) ‘Immunization’ of lipase against acetaldehyde emerging in acyl transfer reactions from vinyl acetate. J Chem Soc, Chem Commun 17:1198–1200

    Article  Google Scholar 

  15. Goto M, Kamiya N, Miyata M, Nakashio F (1994) Enzymatic esterification by surfactant-coated lipase in organic media. Biotechnol Progr 10:263–268

    Article  CAS  Google Scholar 

  16. Huang SY, Chang HL, Goto M (1998) Preparation of surfactant-coated lipase for the esterification of geraniol and acetic acid in organic solvents. Enzym Microb Technol 22:552–557

    Article  CAS  Google Scholar 

  17. Hsieh HJ, Nair GR, Wu WT (2006) Production of ascorbyl palmitate by surfactant-coated lipase in organic media. J Agric Food Chem 54:5777–5781

    Article  CAS  Google Scholar 

  18. Avnir D, Coradin T, Lev O, Livage J (2006) Recent bio-applications of sol–gel materials. J Mater Chem 16:1013–1030

    Article  CAS  Google Scholar 

  19. Vila-Real H, Alfaia AJ, Calado AR, Ribeiro MHL (2010) Improvement of activity and stability of soluble and sol–gel immobilized naringinase in co-solvent systems. J Mol Catal B Enzym 91:91–101

    Article  CAS  Google Scholar 

  20. Yilmaz E (2012) Enantioselective enzymatic hydrolysis of racemic drugs by encapsulation in sol–gel magnetic sporopollenin. Bioprocess Biosyst Eng 35:493–502

    Article  CAS  Google Scholar 

  21. Yang G, Wu JP, Xu G, Yang LR (2009) Improvement of catalytic properties of lipase from Arthrobacter sp. by encapsulation in hydrophobic sol–gel materials. Bioresour Technol 100:4311–4316

    Article  CAS  Google Scholar 

  22. Balamurugan A, Kannan S, Rajeswari S (2003) Synthesis of hydroxyapatite on silica gel surface by using glycerin as a drying control chemical additive. Mater Lett 57:1244–1250

    Article  CAS  Google Scholar 

  23. Desimone MF, Matiacevich SB, Buera MP, Diaz LE (2008) Effects of relative humidity on enzyme activity immobilized in sol–gel-derived silica nanocomposites. Enzym Microb Technol 42:583–588

    Article  CAS  Google Scholar 

  24. Lu SY, Jiang SL, Qian JQ, Guo H (2011) A new trypsin affinity monolithic capillary column prepared from glycerylsilane precursor through sol–gel method. J Liq Chromatogr Relat Technol 34:690–704

    Article  CAS  Google Scholar 

  25. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248–254

    Article  CAS  Google Scholar 

  26. Kamiya N, Goto M, Nakashio A (1995) Surfactant-coated lipase suitable for the enzymatic resolution of menthol as a biocatalyst in organic media. Biotechnol Progr 11:270–275

    Article  CAS  Google Scholar 

  27. Rodgers LE (2005) Effect of sol–gel encapsulation on lipase structure and function: a small angle neutron scattering study. J Sol Gel Sci Technol 33:65–69

    Article  CAS  Google Scholar 

  28. Yi YY, Neufeld R, Kermasha S (2007) Controlling sol–gel properties enhancing entrapped membrane protein activity through doping additives. J Sol Gel Sci Technol 43:161–170

    Article  CAS  Google Scholar 

  29. Shalev M, Miriam A (2011) Sol–gel entrapped levonorgestrel antibodies: activity and structural changes as a function of different polymer formats. Materials 4:469–486

    Article  CAS  Google Scholar 

  30. Mohidem NA, Mat HB (2012) Catalytic activity and stability of laccase entrapped in sol–gel silica with additives. J Sol Gel Sci Technol 61:96–103

    Article  CAS  Google Scholar 

  31. Nirprit SD, Jagdeep K (2002) Immobilization, stability and esterification studies of a lipase from a Bacillus sp. Biotechnol Appl Biochem 36:7–12

    Article  Google Scholar 

  32. Hwang ET, Gu MB (2013) Enzyme stabilization by nano/microsized hybrid materials. Eng Life Sci 13:49–61

    Article  CAS  Google Scholar 

  33. Palomo JM (2009) Modulation of enzymes selectivity via immobilization. Curr Org Synth 6:1–14

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors express their appreciation for the National High Technology Research and Development Program863 (2006AA10Z311), and the Program for Zhejiang Leading Team of S&T Innovation (2010R50032).

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Authors and Affiliations

  1. College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, 310014, People’s Republic of China

    Xiang Zhong, Junqing Qian, Hui Guo, Yuanyuan Hu & Min Liu

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  1. Xiang Zhong
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  2. Junqing Qian
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  3. Hui Guo
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  4. Yuanyuan Hu
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  5. Min Liu
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Correspondence to Junqing Qian.

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Zhong, X., Qian, J., Guo, H. et al. Biosynthesis of sucrose-6-acetate catalyzed by surfactant-coated Candida rugosa lipase immobilized on sol–gel supports. Bioprocess Biosyst Eng 37, 813–818 (2014). https://doi.org/10.1007/s00449-013-1053-9

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  • DOI: https://doi.org/10.1007/s00449-013-1053-9

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