THE FUNCTION OF THE 5-HYDROXYMETHYL GROUP OF LACTOSE IN ENZYMATIC-HYDROLYSIS WITH BETA-GALACTOSIDASE FROM ESCHERICHIA-COLI

被引：11

作者：

ADELHORST, K

BOCK, K

机构：

[1] CARLSBERG LAB,DEPT CHEM,GL CARLSBERG VEJ 10,DK-2500 COPENHAGEN,DENMARK

[2] TECH UNIV DENMARK,DEPT ORGAN CHEM,DK-2800 LYNGBY,DENMARK

来源：

ACTA CHEMICA SCANDINAVICA | 1992年 / 46卷 / 11期

关键词：

D O I：

10.3891/acta.chem.scand.46-1114

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：

A series of 6-substituted methyl lactoside derivatives together with methyl allolactoside and (6S)-methyl [6-H-2]lactoside have been synthesized and characterized by NMR spectroscopy. All compounds were tested as substrates for the enzyme beta-galactosidase from E. coli using progress curve kinetic methology both in single-substrate and competition experiments. The results show that the hydrolysis of methyl lactoside to a large extent takes place through an intramolecular trans-glycosidation reaction via allolactoside. Furthermore, methyl 6-amino-6-deoxy-D-glucopyranoside proved to be an inhibitor for the enzymatic hydrolysis.

引用

收藏

页码：1114 / 1121

页数：8

相关论文

共 24 条

[1] THE SUBSTRATE-SPECIFICITY OF THE ENZYME AMYLOGLUCOSIDASE (AMG) .3. SYNTHESIS OF EPIMERS AND MONO-O-METHYL ETHERS OF METHYL BETA-MALTOSIDE [J].

ADELHORST, K ;

BOCK, K ;

PEDERSEN, H ;

REFN, S .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1988, 42 (03) :196-201

[2] STANNIC TETRACHLORIDE CATALYZED GLYCOSYLATION OF 8-ETHOXYCARBONYLOCTANOL BY CELLOBIOSE, LACTOSE, AND MALTOSE OCTAACETATES - SYNTHESIS OF ALPHA-GLYCOSIDIC AND BETA-GLYCOSIDIC LINKAGES [J].

BANOUB, J ;

BUNDLE, DR .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (16) :2085-2090

[3] 1,2-ORTHOACETATE INTERMEDIATES IN SILVER TRIFLUOROMETHANESULFONATE PROMOTED KOENIGS-KNORR SYNTHESIS OF DISACCHARIDE GLYCOSIDES [J].

BANOUB, J ;

BUNDLE, DR .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (16) :2091-2097

[4] HYDROGENOLYSIS OF CARBOHYDRATE ACETALS KETALS AND CYCLIC ORTHOESTERS WITH LITHIUM ALUMINIUM YDRIDE - ALUMINIUM TRICHLORIDE [J].

BHATTACH.SS ;

GORIN, PAJ .

CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (07) :1195-&

[5] MECHANISM AND BINDING-SPECIFICITY OF BETA-GLUCOSIDASE-CATALYZED HYDROLYSIS OF CELLOBIOSE ANALOGS STUDIED BY COMPETITION ENZYME-KINETICS MONITORED BY H-1-NMR SPECTROSCOPY [J].

BOCK, K ;

SIGURSKJOLD, BW .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1989, 178 (03) :711-720

[6] SYNTHESIS OF DEOXY DERIVATIVES OF LACTOSE AND THEIR HYDROLYSIS BY BETA-GALACTOSIDASE FROM ESCHERICHIA-COLI [J].

BOCK, K ;

ADELHORST, K .

ACTA CHEMICA SCANDINAVICA, 1992, 46 (02) :186-193

[7] ROLE DU LACTOSE ET DE SES PRODUITS METABOLIQUES DANS LINDUCTION DE LOPERON LACTOSE CHEZ ESCHERICHIA COLI [J].

BURSTEIN, C ;

COHN, M ;

KEPES, A ;

MONOD, J .

BIOCHIMICA ET BIOPHYSICA ACTA, 1965, 95 (04) :634-&

[8]

DENNISON JC, 1951, J CHEM SOC, P1616

[9] REACTION OF CARBOHYDRATES WITH METHYLSULFONYL CHLORIDE IN N,N-DIMETHYLFORMAMIDE . PREPARATION OF SOME METHYL 6-CHLORO-6-DEOXYGLYCOSIDES [J].

EVANS, ME ;

LONG, L ;

PARRISH, FW .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (03) :1074-&

[10] SYNTHESIS OF SOME 1,6-ANHYDRO DISACCHARIDES VIA ARYL GLYCOSYL SULFONES [J].

FUNABASHI, M ;

NAGASHIMA, H .

CHEMISTRY LETTERS, 1987, (10) :2065-2068