Czech J. Food Sci., 2010, 28(1):69-73 | DOI: 10.17221/188/2008-CJFS

Improvements in enzymatic preparation of alkyl glycosides

Dagmar Bilaničová1, Vladimír Mastihuba2, Mária Mastihubová2, Jana Bálešová3, Štefan Schmidt3
1 Department of Experimental and Applied Genetics, Slovak Medical University, Bratislava, Slovakia
2 Institute of Chemistry, Center for Glycomics, Slovak Academy of Sciences, Bratislava, Slovakia
3 Institute of Biotechnology and Food Science, Faculty of Chemical and Food Technology, Slovak University of Technology, Bratislava, Slovakia

Three glycosides of middle chain aliphatic alcohols (hexanol and heptanol) were prepared by enzymatic glycosidation. The preparation of hexyl β-D-glucopyranoside was achieved in moderate yields via reverse hydrolysis catalysed by defatted meals from almond, apricot, and peach kernels. The apricot meal as a cheap source of β-glucosidase was found to have catalytic efficiency resembling to that of the almond meal. Hexyl and heptyl β-D-galactopyranosides were prepared from D-lactose by transgalactosidation catalysed by commercial β-galactosidases from Aspergillus oryzae in two-phase system. The improvement of the product yields was achieved by a simple replacement of the organic phase (serving as a pool of acceptor alcohol and extracted product) with a fresh portion of the acceptor.

Keywords: alkyl glycosides; plant seed glycosidases; β-glucosidase; β-galactosidase

Published: February 28, 2010  Show citation

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Bilaničová D, Mastihuba V, Mastihubová M, Bálešová J, Schmidt Š. Improvements in enzymatic preparation of alkyl glycosides. Czech J. Food Sci. 2010;28(1):69-73. doi: 10.17221/188/2008-CJFS.
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References

  1. Amalric C., Lecocu-Michel N. (1997): Concentrate comprising alkyl glycoside mixture and fatty alcohol and corresponding methods of use. US Patent 5670471.
  2. Bradford M.M. (1976): A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding, Analytical Biochemistry, 72: 248-254. Go to original source...
  3. Garcia M.T., Ribosa L., Campos E., Sanchez Leal J. (1997): Ecological properties of alkyglucosides. Chemosphere, 35: 545-556. Go to original source...
  4. Lu W.-Y., Guo-Qiang Lin G.-Q., Yu H.-L., Tong A.-M., Xu J.-H. (2007): Facile synthesis of alkyl β-d-glucopyranosides from d-glucose and the corresponding alcohols using fruit seed meals. Journal of Molecular Catalysis B: Enzymatic, 44: 72-77. Go to original source...
  5. Meezan A., Pillion D.J. (1997): Absorption enhancers for drug administration. US Patent 5661130.
  6. Okahata Y., Mori T. (1998): Transglycosylation catalyzed by a lipid-coated β-d-galactosidase in a twophase aqueous-organic system. Journal of Molecular Catalysis B: Enzymatic, 5: 119-123. Go to original source...
  7. Tong A.M., Lu W.Y., Xu J.H., Lin G.Q. (2004): Use of apple seed meal as a new source of β-glucosidase for enzymatic glucosylation of 4-substituted benzyl alcohols and tyrosol in monophasic aqueous-dioxane medium. Bioorganic and Medicinal Chemistry Letters, 14: 2095-2097. Go to original source... Go to PubMed...
  8. van Rantwijk F., Woudenberg-van Oosterom M., Sheldon R.A. (1999): Glycosidase-catalysed synthesis of alkyl glycosides. Journal of Molecular Catalysis B: Enzymatic, 6: 511-532. Go to original source...
  9. Yu H.-L., Xu J.-H., Lu W.-Y., Lin G.-Q. (2007): Identification, purification and characterization of β-glucosidase from apple seed as a novel catalyst for synthesis of O-glucosides. Enzyme and Microbial Technology, 40: 354-361. Go to original source...
  10. Yu H.-L., Xu J.-H., Lu W.-Y., Lin G.-Q. (2008): Environmentally benign synthesis of natural glycosides using apple seed meal as green and robust biocatalyst. Journal of Biotechnology, 133: 469-477. Go to original source... Go to PubMed...

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