Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides

Abstract

Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl α, β-D-ribofuranosides was assayed. Methyl and ethyl 2,3-di-O-acetyl-α, β-D-ribofuranosides enriched in the α-anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield, respectively, the latter being a new compound. Isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside gave the new isopropyl 2,3-di-O-acetyl-β-D-ribofuranoside in 24% yield. The anomeric substituent affects the regioselectivity of the reaction, since n-propyl and n-butyl α, β-D-ribofuranosides reacted without selectivity.

Keywords::

• Enzymatic alcoholysis
• Candida antarctica B lipase
• regioselectivity
• ribofuranosides

Acknowledgements

AMI and LEI are research members of CONICET. We are grateful to Novozymes (Brazil) for the generous gift of CAL-B.

Declaration of interest: We thank UNQ and SECyT (PICT 06-36472) for financial support. The authors report no conflicts of interest. The authors alone are responsible for the content and writing of the paper.