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

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). Quantit...

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Bibliographic Details
Main Authors: Roncaglia, D.I., Schmidt, A.M., Iglesias, L.E., Iribarren, A.M.
Format: Journal/Newspaper
Language:unknown
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://hdl.handle.net/20.500.12110/paper_01415492_v23_n17_p1439_Roncaglia
Description
Summary: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.

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