2009Indian Journal of Chemistry Section B-organic Chemistry Including Medicinal ChemistryRequires access

Lipase-catalyzed regio- and stereoselective deacylation: Separation of anomers of peracylated α,β-D-ribofuranosides

Raman K. Sharma, Neha Aggarwal, Anu Arya, Carl Erik Olsen, Virinder S. Parmar, Ashok K. Prasad

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Abstract

Efficient regio- and stereoselective deacylation of acyloxy function involving C-5' hydroxyl group of α-anomer over the other similar C-5' acyl group of β-anomer and acyl groups involving secondary hydroxyls in anomeric mixture of peracylates of D-ribose has been achieved during deacylation reaction mediated by Lipozyme® TL IM (Thermomyces lanuginosus lipase immobilized on silica). This enzymatic methodology has been efficiently used for the separation of anomeric mixtures of peracylated α,β-D-ribofuranosides.

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Efficient regio- and stereoselective deacylation of acyloxy function involving C-5' hydroxyl group of α-anomer over the other similar C-5' acyl group of β-anomer and acyl groups involving secondary hydroxyls in anomeric mixture of peracylates of D-ribose has been achieved during deacylation reaction mediated by Lipozyme® TL IM (Thermomyces lanuginosus lipase immobilized on silica). This enzymatic methodology has been efficiently used for the separation of anomeric mixtures of peracylated α,β-D-ribofuranosides.

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Available abstract

Efficient regio- and stereoselective deacylation of acyloxy function involving C-5' hydroxyl group of α-anomer over the other similar C-5' acyl group of β-anomer and acyl groups involving secondary hydroxyls in anomeric mixture of peracylates of D-ribose has been achieved during deacylation reaction mediated by Lipozyme® TL IM (Thermomyces lanuginosus lipase immobilized on silica). This enzymatic methodology has been efficiently used for the separation of anomeric mixtures of peracylated α,β-D-ribofuranosides.

Key concepts: Anomer, Lipase, Stereoselectivity, Chemistry, Catalysis, Organic chemistry, Enzyme, Biocatalysis

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