ENZYMATIC GLYCOSYLATION OF (+ -)-(3,5/4,6)-3,6-DIAZIDO-4,5-DIHYDROXYCYCLOHEXENE - A WAY TO PREPARE STEREOCHEMICALLY PURE AND ENZYME RESISTANT, BASIC PSEUDO-DISACCHARIDES AS COMPETITIVE ENZYME-INHIBITORS/

By beta-D-galactosylation of -)-(3,5/4,6)-3,6-diazido-4,5-dihydroxycyc lohexane, pure -4-O-(beta-D-galactopyranosyl)-5-hydroxycyclohexen (3) was obtained. The diamine 1-O-(beta-D-galactopyranosyl)-2-hydroxycyclo hexane derived from compound 3 by catalytic hydrogenation, is stable a gainst enzymic cleavage and competitively inhibits beta-D-galactosidas e from Escherichia coli with a K-i-value of 5.5 mM. Sigmatropic rearra ngement of 3 in methanolic solution partially led to an unseparable mi xture of the regioisomers o-5-O-(beta-D-galactopyranosyl)-6-hydroxycyc lohexe and -6-O-(beta-D-galactopyranosyl)-5-hydroxycyclohexe. Catalyti c hydrogenation thereof yielded an equally unseparable mixture of the diamines o-3-O-(beta-D-galactopyranosyl)-4-hydroxycyclohexa and -O-(be ta-D-galactopyranosyl)-3-hydroxycyclohexane, inhibiting beta-D-galacto sidase competitively with K-i 0.9 mM.