Earticle

초록

영어

Several glycosidases were reported to produce 2-deoxyglycoside conjugates from glycals and alcoholic or phenolic compound. α-Glucosidase [EC 3.2.1.20, α-D-glucoside glucohydrolase] is a group of typical exo-type carbohydrases, which catalyze the split of α-glucosyl linkage to liberate α-glucose from the non-reducing terminal of substrate. α-Glucosidases belonging to glycoside hydrolase (GH) 13 cannot hydrate D-glucal, but α-glucosidases belonging to GH 31, such as Aspergillus niger, pig serum, rice, buckwheat and sugar beet α-glucosidases, are able to catalyze the hydration of the double bond in D-glucal and produce the α-anomer of 2-deoxyglucose [1]. α-Glucosidase from Aspergillus niger (ANGase) was found to synthesize high yield of the alkyl α-D-2-deoxyglucoside (A2DG) from D-glucal and alkyl alcohols [2, 3]. In this study, the synthetic method of A2DG derivatives was investigated and the structure of product was analyzed. ANGase was much more stable than the tested three enzymes, S. pombe α-glucosidase, pig serum α-glucosidase, and buckwheat α-glucosidase. ANGase maintained the high residual activity was considered to be an enzyme suitable for synthesizing of A2DG in alcoholic solvents. Using ANGase, the optimum reaction conditions in synthesis of methyl α-D-2-deoxyglucoside (M2DG) were investigated with pH (4.0-4.5), temperature (35-35 oC), methanol concentration (70%, v/v), and D-glucal concentration. The 93% of D-glucal was converted into M2DG under the optimum reaction conditions The 14 kinds of A2DG were synthesized and isolated by silica gel column chromatography or liquid/liquid extraction. The yields of ethyl and propyl α-D-2-deoxyglucosides by ANGase in 90% (v/v) ethanol and 1-propanol were 90% and 88%, respectively, and those from alcohols having ling alkyl chain were low yield (83-45%). The structures of 14 kinds of A2DGs were determined to be a-D-2-deoxyglucosides having each alkyl group by MS and NMR analysis, all of which were novel compounds [2, 3]. For high yield production of 2-deoxyglucoside derivatives, the used organic solvents have the two kinds of advantage. During the formation of addition product, alcohols had two kinds function. One is the suppressor of hydration by reduced water molecule; the other function is acted as acceptors by itself in the reaction. It was found that ANGase had four benefits: (1) the simplicity of one step reaction, (2) the high stability in alcohols, (3) its strong addition activity, and (4) the wide acceptability of various alcohols.

저자

• Young-Min Kim [ Laboratory of Functional Carbohydrate Enzymes and Microbial Genomics, School of Biological Sciences and Technology, Chonnam National University, Molecular Enzymology Laboratory, Research Faculty of Agriculture, Hokkaido University ]
• Doman Kim [ Laboratory of Functional Carbohydrate Enzymes and Microbial Genomics, School of Biological Sciences and Technology, Chonnam National University ]
• Kimura A [ Molecular Enzymology Laboratory, Research Faculty of Agriculture, Hokkaido University ]

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간행물

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• 간행물명

  한국생물공학회 학술대회

• 간기

  반년간

• 수록기간

  1985~2013

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  KDC 476 DDC 576