Enzymatic Synthesis of l-Menthyl α-Maltoside and l-Menthyl α-Maltooligosides from l-Menthyl α-Glucoside by Cyclodextrin Glucanotransferase
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概要
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l-Menthyl α-_D-glucopyranosyl-(1→4)-α-_D-glucopyranoside (α-MenG_2), a novel glycoside of l-menthol, was synthesized enzymatically, and its physicochemical properties were characterized. Production of α-MenG_2 from l-menthyl a-_D-glucopyranoside (α-MenG) was attempted since we had already succeeded in the high-yield production of α-MenG using a Xanthomonas campestris enzyme (Nakagawa, H., et al., J. Biosci. Bioeng., 89, 138-144, 2000). Through production tests on enzymes, it was confirmed that cyclodextrin glucanotransferase (CGTase) from Bacillus macerans produced l-menthyl α-_D-maltooligosides (α-MenG_n), containing α-MenG_2, from α-MenG and soluble starch. When 10 ml of a 10 mM citrate-10 mM phosphate buffer (pH 6.0) containing 150 mg of α-MenG, 3 g of soluble starch and CGTase was shaken at 70℃ for 24 h, a total of 81.8% α-MenG was reacted. The molar conversion yields of α-MenG_2 and α-MenG_n with α-glucose degrees of polymerization of 3-18, based on the amount of α-MenG supplied, reached 16.1% and 65.7%, respectively. For efficient production of α-MenG_2, the reaction mixture was treated with α-amylase of Aspergilus oryzae, and α-MenG_n were mainly converted into α-MenG_2: finally, the molar conversion yield of α-MenG_2 reached 74.2% based on the amount of α-MenG supplied, α-MenG_2 was purified and its molecular structure was confirmed by ^<13>C-NMR, ^1H-NMR and two-dimensional HMBC (heteronuclear multiple-bond coherence). α-MenG_2 and its aqueous solution tasted bitter and a little sweet at first, but in a few minutes, a refreshing flavor and sweetness spread. At 20℃ the solubility of a-MenG_2 in pure water was 29.6 g/100 ml, approximately 1570-fold that of α-MenG.
- 社団法人日本生物工学会の論文
- 2002-08-25
著者
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Kino Kuniki
Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University
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Usami Shoji
Department of Molecular Biotechnology, Graduate School of Advanced Sciences of Matter, Hiroshima Uni
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Sato Toshiyuki
Department of Gastroenterological Surgery, Hirosaki University Graduate School of Medicine
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KIRIMURA Kohtaro
Department of Applied Chemistry, School of Science and Engineering, Waseda University
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Kino K
Department Of Applied Chemistry School Of Science And Engineering Waseda University
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Kino Kuniki
Department Of Applied Chemistry Faculty Of Science And Engineering Waseda University
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Kino Kuniki
Department Of Applied Chemistry School Of Science And Engineering Waseda University
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Usami S
Waseda Univ. Tokyo Jpn
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Usami S
Waseda Univ.
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Usami Shoji
Dept. Biol. Fac. Sci. Nagoya Univ.
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DO HIROYUKI
Department of Applied Chemistry, School of Science and Engineering, Waseda University
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Sato Toshiyuki
Department Of Applied Chemistry School Of Science And Engineering Waseda University
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Kino Kuniki
Dep. Of Applied Chemistry Fac. Of Sci. And Engineering Waseda Univ. 3-4-1 Ohkubo Shinjuku-ku Tokyo 1
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Kirimura Kohtaro
Department Of Applied Chemistry Faculty Of Science And Engineering Waseda University
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Usami Shoji
Department Of Applied Chemistry Faculty Of Science And Engineering Waseda University
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Do Hiroyuki
Department Of Applied Chemistry School Of Science And Engineering Waseda University
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