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DOI: 10.1055/s-2005-861821
Synthesis of Modified Purine Nucleosides and Related Compounds Mediated by Adenosine Deaminase (ADA) and Adenylate Deaminase (AMPDA)
Publication History
Publication Date:
03 February 2005 (online)
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Abstract
Adenosine deaminase (ADA) and adenylic acid deaminase (AMPDA) are enzymes that catalyze the hydrolytic deamination of various purine nucleosides. In light of recent reports, ADA and AMPDA may be considered as valuable biocatalysts in nucleoside chemistry. Here, they can find many synthetic applications in the transformation of purine nucleosides that are modified in the base or the ribose moiety. Their use can be extended to carbocyclonucleosides or acyclonucleosides as well.
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1 Introduction
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2 Structure and Catalytic Mechanism of Purine Nucleoside and Nucleotide Deaminases
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2.1 Adenosine Deaminase (ADA)
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2.2 Adenylate Deaminase (AMPDA)
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3 ADA as Biocatalyst
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3.1 Nucleosides with Modifications in the Purine Moiety
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3.2 Adenosines with Modifications in the Furanose Moiety
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3.3 Nucleosides Modified in the Purine and Furanose Moieties
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3.4 Carbocyclonucleosides
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3.5 Acyclonucleosides
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4 AMPDA as Biocatalyst
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4.1 Modified Nucleosides
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4.2 Carbocyclic and Acyclic Nucleosides
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5 Stereochemical Specificity of Deaminating Enzymes
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5.1 Synthetic Nucleosides
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5.2 Carbocyclic and Acyclic Nucleosides
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5.3 Diastereoselectivity of ADA and AMPDA
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6 Concluding Remarks
Key words
adenosine deaminase - adenylate deaminase - nucleosides - carbocyclonucleosides - acyclonucleosides
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