Synthesis of alkyl-α-L-rhamnosides by water soluble alcohols enzymatic glycosylation

Bioresource Technology

Volumn 90, Issue 3, 2003, Pages 297-303

  Martearena, M R ^a   Blanco, S ^a   Ellenrieder, G ^a  

^a UNIVERSIDAD NACIONAL DE SALTA   (Argentina)

Author keywords

Enzymatic glycosylation; Ethyl rhamnoside; Isopropyl rhamnoside; Methyl rhamnoside; Naringin; Propyl rhamnoside; Reverse hydrolysis; Rhamnosidase

Indexed keywords

ALCOHOLS; CHROMATOGRAPHIC ANALYSIS; ENZYME KINETICS; HYDROLYSIS; ION EXCHANGE; NUCLEAR MAGNETIC RESONANCE; PH EFFECTS; SYNTHESIS (CHEMICAL);

GLYCOSYLATION;

BIOTECHNOLOGY;

2 PROPANOL; ALCOHOL DERIVATIVE; AURANTIIN; CARBOHYDRATE DERIVATIVE; FLAVONOID; METHANOL; PROPANOL; RHAMNOSE; WATER;

ARTICLE; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; ENZYME GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PH; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY;

EID: 0142155532     PISSN: 09608524     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-8524(03)00131-7     Document Type: Article

References (30)

1. Benavente Garcia O., Castillo J., Marin F.R., Ortuño A., Del Rio J.A. Uses and Properties of Citrus Flavonoids. J. Agric. Food Chem. 45:1997;4505-4515.
2. Chahid Z., Montet D., Pina M., Graille J. Effect of water activity on enzymatic synthesis of alkylglycosides. Biotechnol. Lett. 14:1992;281-284.
3. Cheetham, P.S.J., Quail, M.A., 1989. Preparation of L-rhamnose from glycosides by enzymic hydrolysis. European Patent EP 88-202595.
4. De Bruyn A., Anteunis M., De Gussem R., Dutton G.G.S. Proton N.M.R. study of L-rhamnose, methyl-α-L-rhamnopyranoside, and 4-O-β-D- galactopyranosyl-L-rhamnose in deuterium oxide. Carbohydr. Res. 47:1976;158-163.
5. Drouet P., Zhang M., Legoy M.D. Enzymatic synthesis of alkyl β-D-xylosides by transxylosylation and reverse hydrolysis. Biotechnol. Bioeng. 43:1994;1075-1080.
6. Ellenrieder G., Daz M. Thermostabilization of naringinase from Penicillium decumbens by proteins in solution and immobilization on insoluble proteins. Biocatal. Biotransform. 14:1996;113-123.
7. Ellenrieder G., Blanco S., Daz M. Hydrolysis of supersaturated naringin solutions by free and immobilized naringinase. Biotechnol.Tech. 12:1998;63-65.
8. Flitsch S.L. Chemical and enzymatic synthesis of glycopolymers. Current Opinion in Chemical Biology. 4:2000;619-625.
9. Gao C.L., Mayon P., MacManus D.A., Vulfson E.N. Novel enzymatic approach to the synthesis of flavonoid glycosides and their esters. Biotechnol.Bioeng. 71:2001;235-243.
10. Gunata, Z., Bitteur, S., Baumes, R., Brillouet, J.M., Tapiero, C., Bayonove, C., Cordonnier, R., 2000. Process for obtaining aroma components and aroma from their precursors of glycosidic nature, and aroma components and aromas thereby obtained. US Patent 6, 106, 872.
11. Ismail A., Ghoul M. Enzymatic synthesis of butylglycosides by glycosidases. Biotechnol. Lett. 18:1996;1199-1204.
12. Kasai R., Okihara M., Asakawa J., Mizutani K., Tanaka O. Carbon-13 NMR study of alpha- and beta-anomeric pairs of D-mannopyranosides and L-rhamnopyranosides. Tetrahedron. 35:1979;1427-1432.
13. Kohchi C., Hayashi M., Nagai S. Purification and properties of β-glucosidase from Candida pelliculosa var. acetaetherius. Agric. Biol. Chem. 49:1985;779-784.
14. Kometani T., Terada Y., Nishimura T., Takii H., Okada S. Transglycosylation to hesperidin by cyclodextrin glucanotransferase from an alkalophilic bacillus species in alkaline pH and properties of hesperidin glycosides. Biosci. Biotechnol. Biochem. 58:1994;1990-1994.
15. Kosary J., Stefanovits-Banyai E., Boross L. Reverse hydrolytic process for O-alkylation of glucose catalyzed by immobilized α- and β-glucosidases. J. Biotechnol. 66:1998;83-86.
16. Lang S., Wullbrandt D. Rhamnose lipids-biosynthesis, microbial production and application potential. Appl. Microbiol. Biotechnol. 51:1999;22-32.
17. Lee S.J., Kim J.C., Kim M.J., Kitaoka M., Park C.S., Lee S.Y., Ra M.J., Moon T.W., Robyt J.F., Park K.H. Transglycosylation of naringin by Bacillus stearothermophilus maltogenic amylase to give glycosylated naringin. J Agr Food Chem. 47:1999;3669-3674.
18. Palcic M.M. Biocatalytic synthesis of oligosaccharides. Curr. Opin. Biotechnol. 10:1999;616-624.
19. Panintrarux C., Adachi S., Araki Y., Kimura Y., Matsuno R. Equilibrium yield of. n -alkyl-β-D-glucoside through condensation of glucose and n -alcohol by β-glucosidase in a biphasic system Enzyme Microb. Technol. 17:1995;32-40.
20. Papanikolaou S. Enzyme-catalyzed synthesis of alkyl-beta-glucosides in a water-alcohol two-phase system. Bioresour. Technol. 77:2001;157-161.
21. Scigelova M., Singh S., Crout D.H.G. Glycosidases-a great synthetic tool. J. Mol. Catal. B: Enzym. 6:1999;483-494.
22. Soares N.F., Hotchkiss J.H. Naringinase immobilization in packaging films for reducing naringin concentration in grapefruit juice. J. Food Sci. 63:1998;61-65.
23. Spagna G., Barbagallo R.N., Martino A., Pifferi P.G. A simple method for purifying glycosidases: α-L-rhamnopyranosidase from Aspergillus niger to increase the aroma of Moscato wine. Enzyme Microb.Technol. 27:2000;522-530.
24. Stevenson D.E., Stanley R.A., Furneaux R.H. Optimization of alkyl β-D-galactopyranoside synthesis from lactose using commercially available β-galactosidases. Biotechnol. Bioeng. 42:1993;657-666.
25. Trincone A., Nicolaus B., Lama L., Morzillo P., De Rosa M., Gambacorta A. Enzyme-catalyzed synthesis of alkyl β-D glycosides with crude homogenate of Sulfolobus solfataricus. Biotechnol. Lett. 13:1991;235-240.
26. van Rantwijk F., Woudenberg-van Oosterom M., Sheldon R.A. Glycosidase-catalyzed synthesis of alkyl glycosides. J. Mol. Catal. B: Enzym. 6:1999;511-532.
27. Vic G., Biton J., Le Beller D., Michel J.M., Thomas D. Enzymatic glucosylation of hydrophobic alcohols in organic medium by the reverse hydrolisis reaction using almond-β-D-glucosidase. Biotechnol. Bioeng. 46:1995;109-116.
28. Vic G., Crout D.H.G. Synthesis of glucosidic derivatives with a spacer arm by reverse hydrolysis using almond β-D-glucosidase. Tetrahedron: Asymmetry. 5:1994;2513-2516.
29. Vulfson E.N., Patel R., Law B.A. Alkyl-β-glucoside synthesis in a water-organic two-phase system. Biotechnol. Lett. 12:1990;397-402.
30. Wymer N., Toone E.J. Enzyme-catalyzed synthesis of carbohydrates. Curr Opin Chem Biol. 4:2000;110-119.