Korean Journal of Microbiology (미생물학회지)

The Microbiological Society of Korea (한국미생물학회)
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Synthesis of Fructose Ester Compound by Lipase in Organic Solvent

유기용매계에서 Lipase에 의한 Fructose Ester의 합성

  • 신영민 (부산대학교 자연과학대학 미생물학과) ;
  • 이상옥 (부산대학교 자연과학대학 미생물학과) ;
  • 이재동 (부산대학교 자연과학대학 미생물학과) ;
  • 이태호 (부산대학교 자연과학대학 미생물학과)
  • Published : 1997.09.01
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Abstract

Sugar ester compounds were synthesized in organic solvent using lipase. Anhydrous pyridinc was selected as ;I solvent because of reasonable solubility of sugar. The synthesis of sugar ester compound was catalyzed by Pseudomonas sp. lipase in the reaction system containing anhydrous pyridine as .i solvent and vinyl butylate as an acyl donor. The analysis of the reaction product by TLC and GC showed thilt monobutyryl and dibutyryl fructose esters were synthesized by transesterification reaction between fructose and vinyl butyrate. Optimal conditions for the transesterification reaction were as follows: the ratio of fructoselvinyl butylate, I : lO(M : M): reaction temperature, 40^{\circ}C.$, velocity of shaking, 150 rprn: concentration of enzyme, 10 mglml. The longer the reaction period, the higher the conversion rate, and the conversion rate reached up to 90% after about 10 days of reaction. Monobutyryl fructose was mainly synthesized in the early stage of reaction, but the amount of dibutyryl fructose increased gradually as the rcdction progressed. When a small amount of water was added to the reaction mixture (micro-water system), the reaction rate decreased, while that of rnonobutyr~l fructosc increased. Only monobutyryl fructose was obtained when 1% water was added to the reaction mixture.

유기용매계에서 lipase AK를 사용하여 당 ester화합물을 합성하였다. 유기용매로는 당의 용해도가 높고 반응성이 뛰어난 pyridine을, acyl donor로는 vinyl butyrate을 선택하였다. Transesterification반응에 의해 생성된 monobutyryl fructose와 dibutyryl fructose는 TLC 및 GC 분석으로 확인하였다. Transesterification에 미치는 반응조건은 fructose:vinyl butyrate의 비가 1:10(M/M), 반응온도 40^{\circ}C.$, 교반속도 150rpm, 효소량 10mg/ml의 경우가 적당하였으며 반응시간이 길어질수록 전환율이 높아져, 반응 10일 정도에서 전환율은 90% 이상에 도달하였다. 이때 반응 초기에는 monobutyryl fructose가 주로 합성되었으나 시간이 경과함에 따라 dibutyryl fructose의 함량비가 증가하였다. 반응계에 소량의 수분을 첨가하였을 경우에는 반응속도가 감소함과 동시에 반응산물중 dibutyryl fructose의 양은 줄어들고 monobutyryl fructose의 생성량이 증가하는 경향을 보여주었으며, 수분함량 1%에서는 monobutyryl fructose만이 생성되었다.

Keywords

References

  1. FEMS Microbiol. Lett. v.3 Bell, G.;J.A. Blain;J.D.E. Paterson;C.E.L. Shaw;R.J. Todd
  2. Biotechnol. v.4 Enzymatic reaction in liquid and solid paraffins Boeriu, C.G.;J.S. Dordick;A.M. Klivanov
  3. Synthesis Esterolytic and lipolytic enzymes in organic synthesis Boland, W.;C. Frobl;M. Lorenz
  4. Carbohydrate analysis: a practical approach Chaplin, M.F.;J.F. Kennedy
  5. Enzyme Microb. Technol. v.11 Enzymatic catalysis in monophasic organic solvent Dordick, J.S.
  6. Biotethnol. Lett. v.9 Production of flavor esters by immobilized lipase Gillies, B.;H. Yamazaki;D.W. Armstrong
  7. Angew. Chem. Int. Ed. Engl. v.28 Enzymatic synthesis of selectively protected glycals Holla, E.W.
  8. Tetrahedron v.42 Enzymatic in organic synthesis Jones, J.B.
  9. Chemtech. v.16 Enzymes that work in organic solvents Klibanov, A.M.
  10. Kor. J. Appl. Microbiol. Bioeng. v.15 Charaterization of lipase in two phase system Kwon, D.Y.;K.H. Kim;J.S. Rhee
  11. Trends Biotechnol. v.4 Solubilization of enzymes in apolar solvents via reverse micellers Luisi, P.L.;C. Laane
  12. J. Am. Chem. Soc. v.109 Peptide synthesis catalyzed by lipases in anhydrous organic solvents Margolin, A.L.;A.M. Klibanov
  13. Biotechnol. Lett. v.9 Lipase catalyzed synthesis of peptides: preparation of a penicilin G precursor and other peptides Matos, J.R.;J.B. West;C.H. Wong
  14. JAOCS v.70 Synthesis of alkylglycoside fatty acid esters in non-aqueous media by Candica sp. lipase Mutua L.N.;C.C. Akoh
  15. Biotechnol. Lett. v.9 Terpene alcohol ester synthesis by polyethylene glycol-modified lipase in Benzene Nishio, T.;K. Takahashi;T. Yoshimoto;Y. Kodera;Y. Saito;Y. Inada
  16. J. Am. Chem. Soc. v.110 Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide Riva, S.;J. Chopineau;A.P.G. Kieboom;A.M. Klibanov
  17. Biotech. Lett. v.15 Lipase catalysed acetylation of carbonhdrates Sharma, A.;S. Chattopadhyay
  18. Biotech. Lett. v.18 Synthesis of biodegradable emulsifier using lipase in anhydrous pyridine Sin, Y.M.;S.H. Chung;J.Y. Park;T.H. Lee
  19. Biotecnol. Lett. Enzymatic synthesis of fructose ester by lipase in anhydrous pyridine Sin, Y.M.;T.H. Lee
  20. J. Am. Chem. Soc. v.85 Gas-liquid chromatography of trimethylsilyl derivatives of sugars and related substances Sweely, C.C.;R. Bentley;M. Makita;W.W. Wells
  21. Agric. Biol. Chem. v.45 Enzymatic acyl exchange of triglycerides in n-hexane Tanaka, T.;E. Ono;M. Ishihara;S. Yamanaka;K. Takinami
  22. J. Am. Chem. Soc. v.108 Facile enzymatic preparation of monoacylated sugars in pyridine Therisod, M.;A.M. Klibanov
  23. J. Am. Chem. Soc. v.109 Regioseletive acylation of secondary hydroxyl groups in sugars catalyzed by lipases in organic solvents Therisod, M.;A.M. Klibanov
  24. J. Am. Chem. Soc. v.110 Lipase-catalyzed irreversible transesterfications using enol esters as acylating reagents:preparative enantio- and regioselective synthesis of alcohols, glycerol derivatives, sugars and organometallics Wang, Y.F.;J.J. Laloned;M. Momogan;D.E. Bergbreiter;C.H. Wong
  25. Nippon Nogeikagaku Kaishi v.65 no.7 Factors affecting activity of enzyme in organic solvent Yamane, T.
  26. Science v.224 Enzymatic catalysis in organic media at 100℃ Zaks, A.;A.M. Klibanov
  27. Proc. Natl. Acad. Sci. U.S.A. v.82 Enzyme-catalyzed processes in organic solvents Zaks, A.;A.M. Klibanov