Collect. Czech. Chem. Commun. 2000, 65, 1619-1629

Porcine Liver Esterase-Catalyzed Hydrolysis of Methyl Tri-O-acetyl-β-D-arabinopyranoside, Methyl Tri-O-acetyl-β-D-ribopyranoside and Methyl Tri-O-acetyl-β-D-ribofuranoside

Jitka Moravcová*, Karel Kefurt, Romana Hladůvková and Jan Staněk

Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague, Czech Republic


Methyl 2,3,4-tri-O-acetyl-β-D-arabinopyranoside (1), methyl 2,3,4-tri-O-acetyl-β-D-ribopyranoside (2), and methyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside (3) were deacetylated in porcine liver esterase-catalyzed reactions. Triacetate 1 gave methyl 3,4-di-O-acetyl-β-D-arabinopyranoside in 70% preparative yield while the regioselectivities found for the substrates 2 and 3 were substantially lower. Both the Michaelis constant and maximum rate were calculated for deacetylation of 1, 2, and 3. The results were interpreted using an active site model for the esterase proposed by Jones.

Keywords: Carbohydrates; Esters; Hydrolases; Biocatalysis; Deacetylation; Enzyme catalysis; Hydrolyses; Protecting groups.

References: 19 live references.