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

• Language: unknown
• Published: 2004
• Subjects: Deacetylation; Enzymatic alcoholysis; Lipases; Nucleosides; Regioselectivity; Alcohols; Catalysis; Alcoholysis; Biotransformation; Enzymes; 2',3',5' tri o acetylcytidine; 3',5' di o acetyl 2' deoxyadenosine; 3',5' di o acetyl 2' deoxycytidine; 3',5' di o acetyl 2' deoxyguanosine; 3',5' di o acetyl 2' deoxyuridine; 3',5' di o acetylthymidine; 4 n acetyl 2',3',5' tri o acetylcytidine; alcohol derivative; cytidine derivative; hydroxyl group; nucleoside derivative; triacylglycerol lipase; unclassified drug; acetylation; Candida antarctica; conference paper; enzyme activity; fungal strain; isomer; stereochemistry; Candida; Antarc*; Antarctica
• Online Access: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v29_n1-6_p129_Zinni; https://hdl.handle.net/20.500.12110/paper_13811177_v29_n1-6_p129_Zinni

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.