Synthesis of Modified Purine Nucleosides and Related Compounds Mediated by Adenosine Deaminase (ADA) and Adenylate Deaminase (AMPDA)

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.

Immobilization of thermostable nucleoside phosphorylases on MagReSyn® epoxide microspheres and their application for the synthesis of 2,6-dihalogenated purine nucleosides

“…Finally, the optimal coimmobilized biocatalysts were used for the synthesis of 2,6-dihalogenated purine nucleosides, and the production yields were optimized. It should be stressed that 2,6-dihalogenated purine nucleosides are valuable precursors for the chemical [20] and enzymatic [21,22] transformations into a large number of base modified nucleosides of medicinal and molecular biological importance. Recently, we have disclosed a high efficiency of the enzymatic transformation of 2,6-dichloropurine (26DCP) and 6-chloro-2-fluoropurine (6C2FP) into their ribo-, 2′-deoxyribo-and arabino-nucleosides employing TtPyNP and GtPNP as biocatalysts of the transglycosylation reaction [23].…”

Concise total synthesis of two marine natural nucleosides: trachycladines A and B

“…In our experiment, ADA failed to give trachycladine A due to its lack of the 5′-hydroxy group, which plays a crucial role for the activity of the enzyme [35]. AMPDA is commercially available as a practical lyophilate powder and was widely used in the food industry for the production of inosine 5′-phosphate.…”

Biocatalysis Applied to the Synthesis of Nucleoside Analogs

“…In the last few years these biocatalysts have shown a great utility in biocatalysis, because they display broad substrate specifi city and their use can also be extended to carbocyclonucleosides and acyclonucleosides [34] . The general process that takes place using these enzymes is outlined in Scheme 10.15 .…”