Enzymatic Production of Alkyl β-Glucoside Based on Transglycosylation Activity of Celluclast

효소적 당전이 반응을 이용한 Alkyl β-Glucoside의 생산

  • Yong, Hwan-Ung (Dept. of Food Science and Nutrition, Hallym University) ;
  • Kim, Seonmi (Dept. of Food Science and Nutrition, Hallym University) ;
  • Shim, Jae-Hoon (Dept. of Food Science and Nutrition, Hallym University)
  • 용환웅 (한림대학교 식품영양학과) ;
  • 김선미 (한림대학교 식품영양학과) ;
  • 심재훈 (한림대학교 식품영양학과)
  • Received : 2012.05.23
  • Accepted : 2012.07.13
  • Published : 2012.10.31


Alkyl glucosides were synthesized using the transglycosylation reaction of Celluclast, the cellulase from Trichoderma reesei, with cellobiose and various alcohols. Glucose as a by-product of the reaction was removed using the immobilized yeast system. Among the alkyl glucoside products, the acceptor products of methanol and ethanol were confirmed as methyl ${\beta}$-D-glucopyranoside and ethyl ${\beta}$-D-glucopyranoside via MALDI-TOF MS and enzymatic analysis. Optimal yields of methyl ${\beta}$-glucoside and ethyl ${\beta}$-glucoside were 65.3% (mol/mol) and 59.0% (mol/mol), respectively, based on cellobiose consumed.


Supported by : 한림대학교


  1. Wang LX, Huang W. 2009. Enzymatic transglycosylation for glycoconjugate synthesis. Curr Opin Chem Biol 13: 592-600.
  2. Bae HK, Lee SB, Park CS, Shim JH, Lee HY, Kim MJ, Baek JS, Roh HJ, Choi JH, Choe EO, Ahn DU, Park KH. 2002. Modification of ascorbic acid using transglycosylation activity of Bacillus stearothermophilus maltogenic amylase to enhance its oxidative stability. J Agric Food Chem 50: 3309-3316.
  3. Lee SJ, Kim JC, Kim MJ, Kitaoka M, Park CS, Lee SY, Ra MJ, Moon TW, Robyt JF, Park KH. 1999. Transglycosylation of naringin by Bacillus stearothermophilus maltogenic amylase to give glycosylated naringin. J Agric Food Chem 47: 3669-3674.
  4. Li D, Park JH, Park JT, Park CS, Park KH. 2004. Biotechnological production of highly soluble daidzein glycosides using Thermotoga maritima maltosyltransferase. J Agric Food Chem 52: 2561-2567.
  5. Park KH, Kim MJ, Lee HS, Han NS, Kim D, Robyt JF. 1998. Transglycosylation reactions of Bacillus stearothermophilus maltogenic amylase with acarbose and various acceptors. Carbohydr Res 313: 235-246.
  6. Cho JS, Yoo SS, Cheong TK, Kim MJ, Kim Y, Park KH. 2000. Transglycosylation of neohesperidin dihydrochalcone by Bacillus stearothermophilus maltogenic amylase. J Agric Food Chem 48: 152-154.
  7. Li D, Roh SA, Shim JH, Mikami B, Baik MY, Park CS, Park KH. 2005. Glycosylation of genistin into soluble inclusion complex form of cyclic glucans by enzymatic modification. J Agric Food Chem 53: 6516-6524.
  8. Vandamme EJ, Soetaert W. 1995. Biotechnical modification of carbohydrates. FEMS Microbiol Rev 16: 163-186.
  9. Thiem J. 1995. Applications of enzymes in synthetic carbohydrate chemistry. FEMS Microbiol Rev 16: 193-211.
  10. Vic G, Biton J, Le Beller D, Michel JM, Thomas D. 1995. Enzymatic glucosylation of hydrophobic alcohols in organic medium by the reverse hydrolysis reaction using almond-$\beta$- D-glucosidase. Biotechnol Bioeng 46: 109-116.
  11. Fischer L, Bromann R, Wagner F. 1995. Enantioselective synthesis of several 1-O-$\beta$-D-glucoconjugates using almond $\beta$-glucosidase (E.C. Biotechnol Lett 17: 1169-1174.
  12. Kim YM, Kim BH, Ahn JS, Kim GE, Jin SD, Nguyen TH, Kim D. 2009. Enzymatic synthesis of alkyl glucosides using Leuconostoc mesenteroides dextransucrase. Biotechnol Lett 31: 1433-1438.
  13. Yan TR, Liau JC. 1998. Synthesis of alkyl $\beta$-glucosides from cellobiose with Aspergillus niger $\beta$-glucosidase II. Biotechnol Lett 20: 653-657.
  14. Yan TR, Lin YH, Lin CL. 1998. Purification and characterization of an extracellular $\beta$-glucosidase II with high hydrolysis and transglucosylation activities from Aspergillus niger. J Agric Food Chem 46: 431-437.
  15. Andric P, Meyer AS, Jensen PA, Dam-Johansen K. 2010. Effect and modeling of glucose inhibition and in situ glucose removal during enzymatic hydrolysis of pretreated wheat straw. Appl Biochem Biotechnol 160: 280-297.
  16. Liu TY, Castelfranco P. 1970. The biosynthesis of ethyl-$\beta$- glucoside in extracts of pea seedlings. Plant Physiol 45: 424-428.
  17. Merino ST, Cherry J. 2007. Progress and challenges in enzyme development for biomass utilization. Adv Biochem Eng Biotechnol 108: 95-120.
  18. Garcia-Aparicio MP, Ballesteros I, Gonzalez A, Oliva JM, Ballesteros M, Negro MJ. 2006. Effect of inhibitors released during steam-explosion pretreatment of barley straw on enzymatic hydrolysis. Appl Biochem Biotechnol 129: 278-288.
  19. Rosgaard L, Andric P, Dam-Johansen K, Pedersen S, Meyer AS. 2007. Effects of substrate loading on enzymatic hydrolysis and viscosity of pretreated barley straw. Appl Biochem Biotechnol 143: 27-40.
  20. Rosgaard L, Pedersen S, Meyer AS. 2007. Comparison of different pretreatment strategies for enzymatic hydrolysis of wheat and barley straw. Appl Biochem Biotechnol 143: 284-296.
  21. Zhang YW, Prabhu P, Lee JK. 2010. Alginate immobilization of recombinant Escherichia coli whole cells harboring L-arabinose isomerase for L-ribulose production. Bioproc Biosyst Eng 33: 741-748.
  22. Baek JS, Kim HY, Abbott TP, Moon TW, Lee SB, Park CS, Park KH. 2003. Acarviosine-simmondsin, a novel compound obtained from acarviosine-glucose and simmondsin by Thermus maltogenic amylase and its in vivo effect on food intake and hyperglycemia. Biosci Biotechnol Biochem 67: 532-539.
  23. Shim JH, Park JT, Hong JS, Kim KW, Kim MJ, Auh JH, Kim YW, Park CS, Boos W, Kim JW, Park KH. 2009. Role of maltogenic amylase and pullulanase in maltodextrin and glycogen metabolism of Bacillus subtilis 168. J Bacteriol 191: 4835-4844.
  24. Lirdprapamongkol K, Svasti J. 2000. Alkyl glucoside synthesis using Thai rosewood $\beta$-glucosidase. Biotechnol Lett 22: 1889-1894.

Cited by

  1. Enzymatic Production of Amylopectin Cluster Using Cyclodextrin Glucanotransferase vol.43, pp.9, 2014,