Anomer-selective glucosylation of l-menthol by yeast α-glucosidase

被引:26
作者
Nakagawa, H
Yoshiyama, M
Shimura, S
Kirimura, K
Usami, S
机构
[1] Waseda Univ, Sch Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, Japan
[2] Lotte Co Ltd, Cent Lab, Urawa, Saitama 3360027, Japan
[3] Waseda Univ, Mat Res Projects Biosci & Photon, Tokyo, Japan
关键词
alpha-glucosidase; menthol; transglucosylation; Saccharomyces cerevisiae;
D O I
10.1271/bbb.62.1332
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
l-Menthol was glucosylated by the alpha-glucosidase (EC 3.2.1.20) of Saccharomyces cerevisiae using maltose as the glucosyl donor. When 50 mg of l-menthol and 1.6 M maltose in 10 mM citrate-phosphate buffer (pH 5.5) were incubated at 45 degrees C, l-menthyl alpha-D-glucopyranoside (alpha-MenG) was alpha-anomer-selectively formed as a product. The specificity of the alpha-linkage was confirmed by C-13-NMR analysis. In the reaction mixture after 2 h, alpha-MenG was mainly accumulated in a crystalline form and the concentration of dissolved alpha-MenG was constant at 1.4 mM. The molar conversion yield of alpha-MenG produced based on the supplied l-menthol was maximally 30.7% at 48 h of reaction.
引用
收藏
页码:1332 / 1336
页数:5
相关论文
共 23 条
[1]   Galactooligosaccharide production by transfer reaction of an exogalactanase [J].
Bonnin, E ;
Thibault, JF .
ENZYME AND MICROBIAL TECHNOLOGY, 1996, 19 (02) :99-106
[2]   ENZYMATIC-SYNTHESIS OF TRISACCHARIDES AND ALKYL BETA-D-GLUCOSIDES BY THE TRANSGLYCOSYLATION REACTION OF BETA-GLUCOSIDASE FROM FUSARIUM-OXYSPORUM [J].
CHRISTAKOPOULOS, P ;
BHAT, MK ;
KEKOS, D ;
MACRIS, BJ .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 1994, 16 (06) :331-334
[3]   ENZYMATIC-SYNTHESIS OF ALKYL BETA-D-XYLOSIDES BY TRANSXYLOSYLATION AND REVERSE HYDROLYSIS [J].
DROUET, P ;
ZHANG, M ;
LEGOY, MD .
BIOTECHNOLOGY AND BIOENGINEERING, 1994, 43 (11) :1075-1080
[4]   ENZYMATIC-SYNTHESIS OF (+)CATECHIN-ALPHA-GLUCOSIDE AND ITS EFFECT ON TYROSINASE ACTIVITY [J].
FUNAYAMA, M ;
NISHINO, T ;
HIROTA, A ;
MURAO, S ;
TAKENISHI, S ;
NAKANO, H .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1993, 57 (10) :1666-1669
[5]   ENZYMATIC-SYNTHESIS OF MONOTERPENYL BETA-D-GLUCOSIDES BY VARIOUS BETA-GLUCOSIDASES [J].
GUNATA, Z ;
VALLIER, MJ ;
SAPIS, JC ;
BAUMES, R ;
BAYONOVE, C .
ENZYME AND MICROBIAL TECHNOLOGY, 1994, 16 (12) :1055-1058
[6]   ENZYME-CATALYZED OLIGOSACCHARIDE SYNTHESIS [J].
ICHIKAWA, Y ;
LOOK, GC ;
WONG, CH .
ANALYTICAL BIOCHEMISTRY, 1992, 202 (02) :215-238
[7]   SYNTHESIS OF ALKYL BETA-MANNOSIDES FROM MANNOBIOSE BY ASPERGILLUS-NIGER BETA-MANNOSIDASE [J].
ITOH, H ;
KAMIYAMA, Y .
JOURNAL OF FERMENTATION AND BIOENGINEERING, 1995, 80 (05) :510-512
[8]   SUBSTRATE-SPECIFICITY AND SUBSITE AFFINITIES OF CRYSTALLINE ALPHA-GLUCOSIDASE FROM ASPERGILLUS-NIGER [J].
KITA, A ;
MATSUI, H ;
SOMOTO, A ;
KIMURA, A ;
TAKATA, M ;
CHIBA, S .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (09) :2327-2335
[9]   ALPHA-D-GLUCOSYL TRANSFER TO PHENOLIC-COMPOUNDS BY SUCROSE PHOSPHORYLASE FROM LEUCONOSTOC-MESENTEROIDES AND PRODUCTION OF ALPHA-ARBUTIN [J].
KITAO, S ;
SEKINE, H .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1994, 58 (01) :38-42
[10]   Synthesis by an alpha-glucosidase of glycosyl-trehaloses with an isomaltosyl residue [J].
Kurimoto, M ;
Nishimoto, T ;
Nakada, T ;
Chaen, H ;
Fukuda, S ;
Tsujisaka, Y .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1997, 61 (04) :699-703