Abstract
Base-labile 6-chloro-2′,3′,5′-tri-O-acetylpurine riboside (1c) and 2-amino-6-chloro-2′,3′,5′-tri-O-acetylpurine riboside (1d) were fully deacetylated through Candida antarctica B lipase hydrolysis, affording respectively 6-chloropurine riboside (2c) and 2-amino-6-chloro-purine riboside (2d). Quantitative results were found at pH 7 and 60 °C in 24 h for 1c and 72 h for 1d. This mild and simple enzymatic technique represents a convenient procedure for the removal of acetyl groups from such base labile halogenated nucleosides.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Barrio JR,Namavari M,Keen RE,Satyamurthy N (1998) The elusive 8-fluoroadenosine. Tetrahedron Lett. 39: 7231-7234.
Brown GB,Weliky VS (1953) The synthesis of 9-β-Dribofuranosylpurine and the identity of nebularine. J. Biol. Chem. 204: 1019-1024.
Ciuffreda P,Casati S,Santaniello E (1999) Lipase-catalysed 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.
Ciuffreda P,Casati S,Santaniello E (2000) The action of adenosine deaminase (E.C. 3.5.4.4.) on adenosine and deoxyadenosine acetates: the crucial role of the 5'-hydroxy group for the enzyme activity. Tetrahedron 56: 3239-3243.
Faber K (1997) Advantages of biocatalysis. In: Biotransformations in Organic Chemistry. Berlin: Springer-Verlag, pp. 3-7.
Ferrero M,Gotor V (2000) Chemoenzymatic transformations in nucleoside chemistry. Monatsch. Chem. 131: 585-616.
Fleysher MH,Bernacki RJ,Bullard GA (1980) Some short-chain N6-substituted adenosine analogues with antitumor properties. J. Med. Chem. 23: 1448-1452.
Iglesias LE,Zinni MA,Gallo M,Iribarren AM (2000) Complete and regioselective deacetylation of peracetylated uridines using a lipase. Biotechnol. Lett. 22: 361-365.
Kazlauskas RJ,Bornscheuer UT (1998) Biotransformations with lipases. In: Rehem HJ,Reed G, eds. Biotechnology, Vol. 8a. Weinheim: VCH, pp. 40-191.
Matzuda A,Shinozaki M,Suzuki M,Watanabe K,Miyasaka T (1986) A convenient method for the selective acylation of guanine nucleosides. Synthesis 385-386.
Nair V,Richardson SG (1980) Utility of purinyl radicals in the synthesis of base-modified nucleosides and alkylpurines: 6-amino group replacement by H, Cl, Br and I. J. Org. Chem. 45: 3969-3974.
Prasad AK,Wengel J (1996) Enzyme-mediated protecting group chemistry on the hydroxyl groups of nucleosides. Nucleos. Nucleot. 15: 1347-1359.
Robins RK (1964) Antitumor activity and structural relationships of purine derivatives and related compounds against neoplasms in experimental animals. J. Med. Chem. 7: 186-199.
Singh HK,Cote GL,Sikorski RS (1993) Enzymatic regioselective deacetylation of 2',3',5'-tri-O-acylribonucleosides: enzymatic synthesis of 2',3'-di-O-acylribonucleosides. Tetrahedron Lett. 34: 5201-5204.
Zemlicka J,Sorm F (1965) Nucleic acids components and their analogs. The reaction of dimethylchloromethyleneammonium chloride with 2',3',5'-tri-O-acetylinosine. A new synthesis of 6-chloro 9-(β-D-ribofuranosyl)purine. Collect. Czech. Chem. Commun. 30: 1880-1889.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Roncaglia, D.I., Schmidt, A.M., Iglesias, L.E. et al. A simple and efficient enzymatic procedure for the deprotection of two base labile chlorinated purine ribosides. Biotechnology Letters 23, 1439–1443 (2001). https://doi.org/10.1023/A:1011615224704
Issue Date:
DOI: https://doi.org/10.1023/A:1011615224704