A simple and efficient enzymatic procedure for the deprotection of two base labile chlorinated purine ribosides

• Language: unknown
• Published: 2001
• Subjects: 2-amino-6-chloropurine riboside; 6-chloropurine riboside; Deacetylation; Lipases; Nucleosides; 2 amino 6 chloropurine riboside; 6 chloropurine ribonucleoside; nebularine; nucleoside; purine derivative; purine nucleoside; triacylglycerol lipase; unclassified drug; article; Aspergillus; Burkholderia cepacia; Candida; catalysis; enzyme activity; hydrolysis; Mucor; nonhuman; thin layer chromatography; Antarc*; Antarctica
• Online Access: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01415492_v23_n17_p1439_Roncaglia; https://hdl.handle.net/20.500.12110/paper_01415492_v23_n17_p1439_Roncaglia

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.