Journal of the Korean Society of Food Science and Nutrition (한국식품영양과학회지)

The Korean Society of Food Science and Nutrition (한국식품영양과학회)
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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
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Abstract

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.

Alkyl-glucoside의 생산을 위하여 상용화 cellulase인 Celluclast의 당전이 반응을 사용하였다. 5가지 종류의 알코올을 acceptor molecule로 하여 반응을 살펴본 결과 methyl alcohol, ethyl alcohol, isopropanol 그리고 butanol에서 당전이 반응이 일어남을 확인하였다. 반응 수율이 높았던, methyl alcohol과 ethyl alcohol의 반응산물을 MALDI-TOF MS와 효소적인 방법을 사용하여 각각의 산물이 methyl ${\beta}$-D-glucopyranoside와 ethyl ${\beta}$-D-glucopyranoside임을 확인하였다. 시간대별 methyl-glucoside와 ethyl-glucoside의 생산량을 비교하여 본 결과 9시간에서 최대 생산 수율 65% (mol/mol)와 59%(mol/mol)를 각각 보였으며, 이후 반응은 진행되지 않았다. Cellulose의 당전이 반응으로 생성된 부산물인 glucose를 제거하기 위하여 고정화 효모 system을 도입하였고, 그 결과 glucose를 모두 제거할 수 있었다. 이상의 결과에서 Celluclast를 이용한 alkyl-glucoside의 생산을 성공적으로 수행하였고, 고정화 효모 system을 도입하여 친환경적으로 부산물을 제거하여 고순도의 ethyl-glucoside를 생산하였다.

Keywords

References

  1. Wang LX, Huang W. 2009. Enzymatic transglycosylation for glycoconjugate synthesis. Curr Opin Chem Biol 13: 592-600. https://doi.org/10.1016/j.cbpa.2009.08.014
  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. https://doi.org/10.1021/jf011550z
  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. https://doi.org/10.1021/jf990034u
  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. https://doi.org/10.1021/jf035109f
  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. https://doi.org/10.1016/S0008-6215(98)00276-6
  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. https://doi.org/10.1021/jf991044y
  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. https://doi.org/10.1021/jf050732g
  8. Vandamme EJ, Soetaert W. 1995. Biotechnical modification of carbohydrates. FEMS Microbiol Rev 16: 163-186. https://doi.org/10.1111/j.1574-6976.1995.tb00164.x
  9. Thiem J. 1995. Applications of enzymes in synthetic carbohydrate chemistry. FEMS Microbiol Rev 16: 193-211. https://doi.org/10.1111/j.1574-6941.1995.tb00283.x
  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. https://doi.org/10.1002/bit.260460204
  11. Fischer L, Bromann R, Wagner F. 1995. Enantioselective synthesis of several 1-O-$\beta$-D-glucoconjugates using almond $\beta$-glucosidase (E.C. 3.2.1.21). Biotechnol Lett 17: 1169-1174. https://doi.org/10.1007/BF00128380
  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. https://doi.org/10.1007/s10529-009-0015-4
  13. Yan TR, Liau JC. 1998. Synthesis of alkyl $\beta$-glucosides from cellobiose with Aspergillus niger $\beta$-glucosidase II. Biotechnol Lett 20: 653-657. https://doi.org/10.1023/A:1005362305545
  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. https://doi.org/10.1021/jf9702499
  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. https://doi.org/10.1007/s12010-008-8512-9
  16. Liu TY, Castelfranco P. 1970. The biosynthesis of ethyl-$\beta$- glucoside in extracts of pea seedlings. Plant Physiol 45: 424-428. https://doi.org/10.1104/pp.45.4.424
  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. https://doi.org/10.1385/ABAB:129:1:278
  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. https://doi.org/10.1007/s12010-007-0028-1
  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. https://doi.org/10.1007/s12010-007-8001-6
  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. https://doi.org/10.1007/s00449-009-0397-7
  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. https://doi.org/10.1271/bbb.67.532
  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. https://doi.org/10.1128/JB.00176-09
  24. Lirdprapamongkol K, Svasti J. 2000. Alkyl glucoside synthesis using Thai rosewood $\beta$-glucosidase. Biotechnol Lett 22: 1889-1894. https://doi.org/10.1023/A:1005696625268

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