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Synthesis and Enzymic Hydrolysis of Acylated Adenosine Derivatives

Various derivatives of adenosine were prepared by acylation of adenosine (6-amino-9-(betha- D-ribofuranosyl)purine (1) with different molar equivalents of acetic anhydride and/or pivaloyl chloride in pyridine. Compounds 6-acetylamino-9-[(2, 3, 5-tri-O-acetyl)-betha-Dribofuranosyl] purine (3), 6-amino-9-[(2, 3, 5-tri-O-acetyl)-betha-D-ribofuranosyl]purine (4), and 6-pivaloylamino-9-[(2, 3, 5-tri-O-pivaloyl)-betha-D-ribofuranosyl]purine (5) were subsequently submitted to hydrolysis catalyzed by a number of hydrolytic enzymes. Regioselective enzymic deacetylation at the primary hydroxyl group of 3 and 4 with butyrylcholinesterase (BChE) produced 6-acetylamino-9-[(2, 3-di-O-acetyl)-betha-D-ribofuranosyl] purine (9) and 6-amino-9-[(2, 3-di-O-acetyl-betha-D-ribofuranosyl]purine (10), respectively. All structures were established by 1H and 13C NMR spectroscopies.

Acylated adenosine; Hydrolases; Enzymic hydrolysis

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