Abstract
Nucleoside phosphorylases (NPs) are transferases that catalyse the reversible cleavage of the glycosidic bond of ribo- or deoxyribo nucleosides, in the presence of inorganic phosphate, to generate the base and ribose- or deoxyribose- 1-phosphate. Since pyrimidine as well as purine nucleoside phosphorylases exist, the combination of both enzymes makes possible the generation of purine nucleosides from pyrimidine ones. As a consequence, NPs from different sources, mainly bacterial, have been exploited as tools for the enzymatic synthesis of nucleoside analogues. These molecules are extensively used as antiviral and anticancer agents because of their ability to act as reverse transcriptase inhibitors or chain terminators in RNA or DNA synthesis. This review covers literature reports from 2000 on, focused mainly on the synthesis of nucleosides by free and immobilised microbial whole cells, along with some examples of modified nucleosides obtained by coupling transglycosylation to other enzymatic reactions. The biological aspects of NPs are also discussed since they became an interesting target for clinical applications due to their key role in nucleotide metabolism. Finally, brief comments about their structures and catalytic mechanisms are included.
Keywords: Azanucleosides, Glycosyltransfer Reaction, NP-I family, TP-catalysed phosphorolysis, Immobilisation, Coupled Enzymatic Systems
Current Organic Chemistry
Title: Nucleoside Phosphorylases
Volume: 10 Issue: 11
Author(s): E. S. Lewkowicz and A. M. Iribarren
Affiliation:
Keywords: Azanucleosides, Glycosyltransfer Reaction, NP-I family, TP-catalysed phosphorolysis, Immobilisation, Coupled Enzymatic Systems
Abstract: Nucleoside phosphorylases (NPs) are transferases that catalyse the reversible cleavage of the glycosidic bond of ribo- or deoxyribo nucleosides, in the presence of inorganic phosphate, to generate the base and ribose- or deoxyribose- 1-phosphate. Since pyrimidine as well as purine nucleoside phosphorylases exist, the combination of both enzymes makes possible the generation of purine nucleosides from pyrimidine ones. As a consequence, NPs from different sources, mainly bacterial, have been exploited as tools for the enzymatic synthesis of nucleoside analogues. These molecules are extensively used as antiviral and anticancer agents because of their ability to act as reverse transcriptase inhibitors or chain terminators in RNA or DNA synthesis. This review covers literature reports from 2000 on, focused mainly on the synthesis of nucleosides by free and immobilised microbial whole cells, along with some examples of modified nucleosides obtained by coupling transglycosylation to other enzymatic reactions. The biological aspects of NPs are also discussed since they became an interesting target for clinical applications due to their key role in nucleotide metabolism. Finally, brief comments about their structures and catalytic mechanisms are included.
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Cite this article as:
Lewkowicz S. E. and Iribarren M. A., Nucleoside Phosphorylases, Current Organic Chemistry 2006; 10 (11) . https://dx.doi.org/10.2174/138527206777697995
DOI https://dx.doi.org/10.2174/138527206777697995 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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