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Enzymatic synthesis of alkyl α-2-deoxyglucosides by alkyl alcohol resistant α-glucosidase from Aspergillus niger
Institution:1. Institute of Automation and Control Processes FEB RAS, 5 Radio Street, 690041 Vladivostok, Russia;2. School of Natural Sciences, Far Eastern Federal University, 690950 Vladivostok, Russia;3. Institute of Atomic and Molecular Sciences, Academia Sinica, P.O. Box 23-166, Taipei, Taiwan;4. Department of Electronics, Vladivostok State University of Economics and Service, 690600 Vladivostok, Russia
Abstract:Aspergillus niger α-glucosidase (ANGase) was used for an efficient syntheses of alkyl α-d-2-deoxyglucosides (A2DGs) and for regioselectivity studies of alkoxy-hydro additions of d-glucal in the presence of alkyl alcohols. ANGase showed a high stability with respect to the high concentration of alkyl alcohols. The reaction conditions were optimized for pH, temperature, alkyl alcohol concentration, and d-glucal concentration. On the basis of MS and NMR analyses, A2DGs were confirmed to have only an α-2-deoxyglucosidic bond and the two-dimensional NMR (HMBC) spectra showed to be made up of 2-deoxyglucosyl and alkyl moieties.
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