Derivatives of methyl beta-lactoside as substrates for and inhibitors of beta-D-galactosidase from E. coli.
The 2'-,4'-, and 6'-deoxy derivatives of methyl beta-lactoside have been synthesised by deoxygenation at positions 2', 4', and 6', and the 3'-deoxy derivative was obtained by a glycosylation reaction. The 2'-O-methyl, 2'-O-benzyl, 2'-amino-2'-deoxy, and 1'-deuterio derivatives have been synthesized also. Only the 6'-deoxy and 1'-deuterio derivatives were substrates for the beta-D-galactosidase from E. coli, and the 2'-deoxy- and 2'-amino-2'-deoxy derivatives were potent inhibitors for the hydrolysis of methyl beta-lactoside by the enzyme.
Bock
K
K
Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark.
Adelhorst
K
K
D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D004926:Escherichia coli / Q000201:enzymology; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008759:Methylglycosides / Q000737:chemistry / Q000494:pharmacology*; D008969:Molecular Sequence Data; D013379:Substrate Specificity; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors / Q000378:metabolism*
D008759:Methylglycosides; C034207:methyl lactoside; D001616:beta-Galactosidase