Effect of acyl chain length on selective biocatalytic deacylation on O-aryl glycosides and separation of anomers

•Lipozyme® TL IM catalyzed separation of anomers of O-aryl α,β-D-ribofuranoside is demonstrated.•Biocatalytic selective deacylation of C-5′-O-acyloxy group of α-anomer in α,β-mixture has been achieved.•The reaction time of deacylation decreases with increase in the acyl chain length.•Easy synthesis of α- and β-anomers of O-aryl D-ribofuranosides has been carried out.

It has been demonstrated that Lipozyme® TL IM (Thermomyces lanuginosus lipase immobilised on silica) can selectively deacylate the ester function involving the C-5′ hydroxyl group of α-anomers over the other acyl functions of anomeric mixture of peracylated O-aryl α,β-D-ribofuranoside. The analysis of results of biocatalytic deacylation reaction revealed that the reaction time decreases with the increase in the acyl chain length from C1 to C4. The unique selectivity of Lipozyme® TL IM has been harnessed for the separation of anomeric mixture of peracylated O-aryl α,β-D-ribofuranosides, The lipase mediated selective deacylation methodology has been used for the synthesis of O-aryl α-D-ribofuranosides and O-aryl β-D-ribofuranosides in pure forms, which can be used as chromogenic substrate for the detection of pathogenic microbial parasites containing glycosidases.

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