Synthesis of deoxy derivatives of lactose and their hydrolysis by beta-galactosidase from E. coli.
Methyl 2-deoxy-alpha-lactoside, methyl 3-deoxy-beta-lactoside, 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol and the 2-deoxy and 2,3-dideoxy derivatives of 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol have been synthesized by deoxygenation of lactose derivatives at appropriate positions. Cyclohexyl beta-D-galactopyranoside has also been synthesized. All derivatives proved to be substrates for the enzyme beta-galactosidase from E. coli, but the rate of hydrolysis of the substrate analogues was strongly dependent on the nature of the aglycone.
Bock
K
K
Department of Chemistry, Carlsberg Laboratory, Copenhagen, Valby, Denmark.
Adelhorst
K
K
D002240:Carbohydrate Sequence; D004926:Escherichia coli / Q000201:enzymology*; D006868:Hydrolysis; D007785:Lactose / Q000031:analogs & derivatives* / Q000378:metabolism; D008969:Molecular Sequence Data; D001616:beta-Galactosidase / Q000378:metabolism*
D001616:beta-Galactosidase; D007785:Lactose