Collect. Czech. Chem. Commun. 2006, 71, 769-787

Adenosine Deaminase in Nucleoside Synthesis. A Review

Mukta Gupta and Vasu Nair*

Department of Pharmaceutical and Biomedical Sciences and The Center for Drug Discovery, The University of Georgia, Athens, GA 30602, U.S.A.


Adenosine deaminase (ADA) is an enzyme in the purine salvage pathway that catalyzes the deamination of adenosine and deoxyadenosine to inosine and deoxyinosine, respectively. This deamination is an important factor in limiting the usefulness of adenosine analogues in chemotherapy. However, the biocatalysis by ADA is also a useful transformation in enzymatic synthesis. In this review, examples from both the principal investigator's laboratory and from the literature, which depict the synthetic usefulness of this enzyme in deamination, dehalogenation, demethoxylation reactions and in diastereoisomeric resolution, are presented. It is not the intent of this review to comprehensively list all of the biotransformations induced by adenosine deaminase, but rather to present representative examples to highlight the powerful synthetic utility of this enzyme. A review with 72 references.

Keywords: Adenosine deaminase; Nucleosides; Enzyme catalysis; Deamination; Hydrolysis; Dechlorination; Adenosine; Inosine; Nucleoside analogues; Antiviral activity.

References: 72 live references.