Abstract
Two new compounds, 2′,3′-di-O-ethoxycarbonyluridine and 2′,3′-di-O-ethoxycarbonylinosine, were obtained through a Candida antarctica lipase B catalysed regioselective ethanolysis of the corresponding trialcoxycarbonylated nucleosides with benzyl alcohol in 1,4-dioxane at 30°C.
Similar content being viewed by others
References
Bornscheuer U, Kazlauskas R (1999) Hydrolases in organic chemistry, Wiley-VCH, Weinheim
Capello M, González M, Rodríguez SD, Iglesias LE, Iribarren AM (2005) A mild and quantitative procedure for the removal of alkoxycarbonyl groups using pig liver esterase or Candida antarctica B lipase. J Mol Catal B Enzym 36:36–39
Ferrero M, Gotor V (2000) Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides and C-nucleosides. Chem Rev 100:4319–4348
Hacking MAPJ, Van Rantwijk F, Sheldon RA (2000) Lipase catalysed reactions of aliphatic and arylaliphatic carbonic acid esters. J Mol Catal B Enzym 9:201–208
Iglesias LE, Zinni MA, Gallo M, Iribarren AM (2000) Complete and regioselective deacetylation of peracetylated uridines using a lipase. Biotechnol Lett 22:361–365
Kadereit D, Waldmann H (2001) Enzymatic protecting group techniques. Chem Rev 101:3367–3396
Parrish JP, Salvatore RN, Jung KW (2000) Perspectives on alkyl carbonates in organic synthesis. Tetrahedron 56:8207–8237
Whalen LJ, Morrow CJ (2000) Resolution of a chiral alcohol through lipase-catalyzed transesterification of its mixed carbonate by poly(ethylene glycol) in organic media. Tetrahedron: Asymmetry 11:1279–1288
Zinni MA, Iglesias LE, Iribarren AM (2002) Regioselective preparation of 2′,3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis. Biotechnol Lett 24:979–983
Zinni MA, Rodríguez SD, Pontiggia RM, Montserrat JM, Iglesias LE, Iribarren AM (2004) Enzymatic alcoholysis of 3′,5′-di-O-acetyl-2′-deoxynucleosides. J Mol Catal B Enzym 29:129–132
Zinni MA, Aljinovic EM, Iglesias LE, Iribarren AM (2004) Optimisation of the lipase-catalysed preparation of a nucleoside prodrug model using an experimental design methodology. Quim Nova 27:496–498
Acknowledgements
We thank UNQ, CONICET, SECyT and CIC for partial financial support. LEI and AMI are research members of CONICET. We are grateful to Novozymes (Brazil) for the generous gift of CAL B.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Capello, M., Imanishi, L., Iglesias, L.E. et al. Two new dialkoxycarbonylated nucleosides obtained through a regioselective enzymatic alcoholysis. Biotechnol Lett 29, 1217–1220 (2007). https://doi.org/10.1007/s10529-007-9374-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10529-007-9374-x