Regioselective Enzymatic Hydrolysis of 3',5'-DI-O-Acetylthymidine and Observation of a Surface Effect Due to Polystyrene |
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Authors: | David H G Crout Alicia M Dachs Susan E Glover David W Hutchinson |
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Institution: |
a Department of Chemistry, University of Warwick, England, UK |
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Abstract: | The selective enzymatic hydrolysis of 3',5'-di-O-acetylthyidine (1) was studied. The lipases from porcine pancreas and Aspergillus niger, and pig liver esterase, all catalysed selective hydrolysis of the 5'O-acetyl group, but the lipase from Candida cylindracea catalysed selective hydrolysis of the 3'-O-acetyl group. Highest selectivity, leading to essentially pure 3'-O-acetylthymidine, was achieved using porcine pancreatic lipase in dilute solution at pH 7.5. Provision of an artificial interface in the form of polystyrene beads led to a significant increase in the rate of hydrolysis, accompanied by a marked fall in selectivity. Other changes in the hydrolysis conditions, such as raising the concentration of substrate or adding cosolvent, also led to a fall in selectivity. |
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Keywords: | Biotransformation nucleosides 3' 5'-di-O-acetylthymidine 3'-O-acetylthymidine lipase esterase porcine pancreatic lipase pig liver esterase Aspergillus niger Candida cylindracea ester hydrolysis |
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