Derivatives of methyl β-lactoside as substrates for and inhibitors of β- d-galactosidase from E. coli

Abstract

The 2′-, 4′-, and 6′-deoxy derivatives of methyl β-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 β- d-galactosidase from E. coli, and the 2′-deoxy- and 2′-amino-2′-deoxy derivatives were potent inhibitors for the hydrolysis of methyl β-lactoside by the enzyme.