Enzymatic alcoholysis of 3’,5’-di-O-acetyl-2’-deoxynucleosides

MARIA A ZINNI; SILVIO D. RODRÍGUEZ; RODRIGO M. PONTIGGIA; JAVIER M. MONTSERRAT; LUIS E. IGLESIAS; ADOLFO M. IRIBARREN

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC

Elsevier

Año: 2004 vol. 29 p. 129 - 132

1381-1177

Candida antarctica-B (CAL-B) lipase-catalysed alcoholysis of a set of 3 ,5 -di-O-acetyl-2 -deoxynucleosides (1a–e) gave the corresponding 3 -O-acetyl-2 -deoxy-nucleosides (2a–e) in yields ranging from 50 to 96%. The alcohol employed in the biotransformation affected the rate of the enzymatic reaction and the yield of the 3 -O-acetylated product, but in all cases only this regioisomer was formed. The obtained results are in agreement with the regioselectivity displayed by CAL-B lipase in previously reported biotransformations of nucleosides. CAL-B catalysed alcoholysis of 2 ,3 ,5 -tri-O-acetyl-cytidine and 4-N-acetyl-2 ,3 ,5 -tri-O-acetylcytidine was also studied, affording with the same regioselectivity the corresponding free 5 -hydroxyl nucleosides. © 2004 Elsevier B.V. All rights reserved.