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 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. © 1990.