Enzymes in Carbohydrate Synthesis: Lipase-Catalyzed Selective Acylation and Deacylation of Furanose and Pyranose Derivatives

Article abstract of DOI:10.1021/jo00256a008

A number of furanose and pyranose derivatives were selectively acylated and deacylated on a preparative scale in lipase-catalyzed reactions.The primary hydroxyl functions of the methyl furanosides of D-ribose, D-arabinose, D-xylose, and 2-deoxy-D-ribose were selectively acetylated by crude porcine pancreatic lipase in tetrahydrofuran by using 2,2,2-trifluoroethyl acetate as the acyl donor.Selective deacetylations of the primary hydroxyl functions in the peracetylated methyl furanosides of D-ribose, D-arabinose, D-xylose, and 2-deoxy-D-ribose were best accomplished in a 9:1 solution of 0.1 N phosphate buffer (pH 7) and N,N-dimethylformamide using Candida cylindracea lipase.Selective cleavage of the 1-O-acetyl groups from 1,2,3,5-tetra-O-acetyl-D-ribose and -D-xylose were similarly accomplished with Aspergillus niger lipase.Similar regioselectivites were observed in the pyranose series.The Candida lipase was found to be the best for selective deacylation of the primary position from the peracylated methyl pyranosides, and porcine pancreatic lipase was the best for selective hydrolysis of the 1-O-acetyl groups from peracetylated pyranoses.