Disease relevance of d-Galactal

• Evaluation of C-(beta-D-galactosyl) and C-(2-deoxy-D-lyxo-hex-1-enopyranosyl) (D-galactal type) derivatives as inhibitors of beta-D-galactosidase from Escherichia coli [1].

High impact information on d-Galactal

• Comparison of the beta-galactosidase conformations induced by D-galactal and by magnesium ions [2].
• [reaction: see text] The reaction of the new D-galactal-derived allylic aziridine 1beta with O-nucleophiles (alcohols and monosaccharides) affords, in a high to complete beta-stereoselectivity, the corresponding 2,3-unsaturated-beta-O-glycosides bearing a beta-N-functionality at C4 [3].
• The protocol has as a key step a novel oxocarbenium ion-enol ether cyclization to give a C1-substituted galactal [4].
• The hydration of D-galactal by the alpha-galactosidase in D2O yielded 2-deoxy-2(S)-D-[2-2H]galactose; the hydration of D-[2-2H]galacto-octenitol in H2O yielded 1,2-dideoxy-2(R)-D-[2-2H]galactooct-3-ulose [5].
• Syntheses of higher acyclic nitrogen containing deoxy sugar derivatives via nitroaldol reaction of different nitroalkanes with 2,3-dideoxy-alpha,beta-unsaturated aldehydo sugars obtained from glycals namely acetylated glucal and galactal and their in vitro antimycobacterial activity are presented [6].

Associations of d-Galactal with other chemical compounds

• The results strongly suggest that there has to be either an equatorial hydroxyl at the 2 position of a sugar or a special reactivity (as with D-galactal) in order for the enzyme to catalyze the beta-galactosidase reaction [7].
• The stereochemistry of the addition of glycerol to D-galactal, catalyzed by beta-D-galactosidase [8].

References