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

Author:

Ciuffreda Pierangela,Casati Silvana,Santaniello Enzo

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference24 articles.

1. (a) Cory, J. G.; Suhadolnik, R. J. Biochemistry 1965, 4, 1729–1732.

2. (b) Cory, J. G.; Suhadolnik, R. J. Biochemistry 1965, 4, 1733–1735.

3. Lipophilic, Acid-Stable, Adenosine Deaminase-Activated Anti-HIV Prodrugs for Central Nervous System Delivery. 2. 6-Halo- and 6-Alkoxy Prodrugs of 2'-.beta.-Fluoro-2',3'-dideoxyinosine

4. Lipase-catalyzed protection of the hydroxy groups of the nucleosides inosine and 2′-deoxyinosine: A new chemoenzymatic synthesis of the antiviral drug 2′,3′-dideoxyinosine

5. In a different synthetic approach, we started from inosine 2 and unsuccessfully tried to prepare the classical 2′,3′-O-(methoxymethylene) derivative that was needed for further elaboration. Due to insolubility of 2 in the reaction medium, poor yields of the required compound were obtained using trimethylorthoformate as reagent and solvent, whereas addition of DMSO or DMF improved the yields but complicated the work-up.

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