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densitometer. Yields are given on the basis of HPTLC
method (Table 4).
4.2.3. In preparative-scale reactions in 1,2-diacetoxy-
ethane of 10% water content as solvent. Reaction
mixtures (5 ml) containing immobilized b-glucosidase
(30 mg), glucose (0.18 g, 1 mmol) and hydroxy compound
(20 mmol) in 1,2-diacetoxyethane of 10% water content
were shaken on IKA-VIBRAX-VXR shaker at speed
200 min21 at room temperature for 6 days. Immobilized
enzyme was filtered off and washed three times with
distillated water (5 ml). The isolation of glycosides by
evaporation of filtrate in vacuo and preparative layer
chromatography of residue on Kieselgel PF254 layer by
chloroform–ethyl acetate–methanol mixtures as eluants
gave pure O-alkyl and aryl b-D-glucosides.
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All of O-alkyl and aryl b-D-glucosides synthesized in
preparative-scale are known in the literature and they were
identified by the authentic samples. Their optical purity was
controlled by their 1H-NMR spectra according to the
literature20 (d 4.50–4.56 ppm 1 H, d, 1-H). 1H-NMR
spectra were taken on a Varian EM-390 90 MHz instrument
using TMS as internal standard in DMSO-d6. Yields after
isolation are given in parentheses.
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O-n-Butyl b-D-glucopyranoside15 (15%);
O-n-Pentyl b-D-glucopyranoside21 (17%);
O-n-Hexyl b-D-glucopyranoside11 (19%);
O-Cyclohexyl b-D-glucopyranoside21 (19%);
O-n-Octyl b-D-glucopyranoside10 (18%);
O-n-Nonyl b-D-glucopyranoside10 (16%);
O-n-Decyl b-D-glucopyranoside10 (12%);
O-Phenyl b-D-glucopyranoside22 (13%);
O-4-Nitrophenyl b-D-glucopyranoside23 (11%).
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This research is a participant of Cost Action D25 ‘Applied
Biocatalysis: Stereoselective and Environmentally Friendly
Reactions Catalyzed by Enzymes’.
References and notes
1. Farber, K.; Franssen, M. C. Trends Biotechnol. 1993, 13,
63–70.