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Complete and regioselective deacetylation of peracetylated uridines using a lipase

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Abstract

Lipase-catalysed alcoholysis and hydrolysis of 2′,3′,5′-tri-O-acetyluridine (1a) and 2′,3′,5′-tri-O-acetyl-2′-C-methyluridine (1b) were studied. Conditions for full and regioselective deacetylation of 1aand 1b are shown in the present work. New compound 2′,3′-di-O-acetyl-2′-C-methyluridine (3b) was prepared by regioselective lipase-catalysed deacetylation.

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References

  • Brown GB, Weliky VS (1953) The synthesis of 9-β-Dribofuranosylpurine and the identity of nebularine. J. Biol. Chem. 204: 1019-1024.

    Google Scholar 

  • Ciuffreda P, Casati S, Santaniello E (1999) Lipase-catalyzed protection of the hydroxy groups of the nucleosides inosine and 2′-deoxyinosine: a new chemoenzymatic synthesis of the antiviral drug 2′,3′-dideoxyinosine. Bioorg. Med. Chem. Lett. 9: 1577-1582.

    Google Scholar 

  • Conde S, Esteban AI, Alonso D, Lopez-Serrano P, Martinez A (1998) Enzymatic alcoholysis of SO2-uracil analog diacyclonucleosides. Long-distance effect of the substituents on the regioselectivity. J. Mol. Cat. B: Enzymatic 4: 295-302.

    Google Scholar 

  • Drauz K, Waldmann H, eds. (1995) Hydrolysis and formation of CO bonds. In: Enzyme Catalysis in Organic Synthesis. Weinheim: VCH, pp. 251-261.

  • Faber K (1995) Advantages of biocatalysts. In: Biotransformations in Organic Chemistry. Berlin: Springer-Verlag, pp. 3-7.

    Google Scholar 

  • Hanrahan JR, Hutchinson DW (1992) The enzymatic synthesis of antiviral agents. J. Biotech. 23: 193-210.

    Google Scholar 

  • Kazlauskas RJ, Bornscheuer UT (1998) Biotransformations with lipases. In: Rehem HJ, Reed G, eds. Biotechnology, Vol 8a. Weinheim: VCH, pp. 40-191.

    Google Scholar 

  • Jones RA (1985) Preparation of protected deoxyribonucleosides. In: Gait MJ, ed. Oligonucleotide Synthesis: A Practical Approach. Oxford: IRL Press, pp. 23-33.

    Google Scholar 

  • Perigaud C, Gosselin G, Imbach JL (1992) Nucleosides analogues as chemotherapeutic agents: a review. Nucleosides Nucleotides 11: 903-945.

    Google Scholar 

  • Ritzmann G, Klein RS, Hollenberg DH, Fox JJ (1975) Nucleosides LXXXIX. Synthesis of 1-(2-chloro-2-deoxy-α-and-β-Darabinofuranosyl) cytosines. Carbohydr. Res. 39: 227-236.

    Google Scholar 

  • Sanfilippo C, Patti A, Piatelli M, Nicolosi G (1997) An efficient enzymatic preparation of (+) and (-) conduritol E, a cyclitol with C 2 symmetry. Tetrahedron: Asymm. 8: 1569-1573.

    Google Scholar 

  • Singh HK, Cote GL, Sikorski RS (1993) Enzymatic regioselective deacylation of 2′,3′, 5′-tri-O-acylribonucleosides: enzymatic synthesis of 2′,3′-di-O-acylribonucleosides. Tetrahedron Lett. 34: 5201-5204.

    Google Scholar 

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Iglesias, L.E., Zinni, M.A., Gallo, M. et al. Complete and regioselective deacetylation of peracetylated uridines using a lipase. Biotechnology Letters 22, 361–365 (2000). https://doi.org/10.1023/A:1005620617554

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  • DOI: https://doi.org/10.1023/A:1005620617554

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