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Two new dialkoxycarbonylated nucleosides obtained through a regioselective enzymatic alcoholysis

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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.

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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

    Article  CAS  Google Scholar 

  • Ferrero M, Gotor V (2000) Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides and C-nucleosides. Chem Rev 100:4319–4348

    Article  PubMed  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Iglesias LE, Zinni MA, Gallo M, Iribarren AM (2000) Complete and regioselective deacetylation of peracetylated uridines using a lipase. Biotechnol Lett 22:361–365

    Article  CAS  Google Scholar 

  • Kadereit D, Waldmann H (2001) Enzymatic protecting group techniques. Chem Rev 101:3367–3396

    Article  PubMed  CAS  Google Scholar 

  • Parrish JP, Salvatore RN, Jung KW (2000) Perspectives on alkyl carbonates in organic synthesis. Tetrahedron 56:8207–8237

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    CAS  Google Scholar 

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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.

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Correspondence to Luis E. Iglesias.

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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

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  • DOI: https://doi.org/10.1007/s10529-007-9374-x

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