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Journal articles on the topic 'Nucleoside phosphorylases'

Author: Grafiati

Published: 7 June 2025

Last updated: 2 August 2025

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1

PUGMIRE, Matthew J., and Steven E. EALICK. "Structural analyses reveal two distinct families of nucleoside phosphorylases." Biochemical Journal 361, no. 1 (2001): 1–25. http://dx.doi.org/10.1042/bj3610001.

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The reversible phosphorolysis of purine and pyrimidine nucleosides is an important biochemical reaction in the salvage pathway, which provides an alternative to the de novo purine and pyrimidine biosynthetic pathways. Structural studies in our laboratory and by others have revealed that only two folds exist that catalyse the phosphorolysis of all nucleosides, and provide the basis for defining two families of nucleoside phosphorylases. The first family (nucleoside phosphorylase-I) includes enzymes that share a common single-domain subunit, with either a trimeric or a hexameric quaternary struc

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2

Il’icheva, Irina A., Konstantin M. Polyakov, and Sergey N. Mikhailov. "Strained Conformations of Nucleosides in Active Sites of Nucleoside Phosphorylases." Biomolecules 10, no. 4 (2020): 552. http://dx.doi.org/10.3390/biom10040552.

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Nucleoside phosphorylases catalyze the reversible phosphorolysis of nucleosides to heterocyclic bases, giving α-d-ribose-1-phosphate or α-d-2-deoxyribose-1-phosphate. These enzymes are involved in salvage pathways of nucleoside biosynthesis. The level of these enzymes is often elevated in tumors, which can be used as a marker for cancer diagnosis. This review presents the analysis of conformations of nucleosides and their analogues in complexes with nucleoside phosphorylases of the first (NP-1) family, which includes hexameric and trimeric purine nucleoside phosphorylases (EC 2.4.2.1), hexamer

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3

Lewkowicz, E., and A. Iribarren. "Nucleoside Phosphorylases." Current Organic Chemistry 10, no. 11 (2006): 1197–215. http://dx.doi.org/10.2174/138527206777697995.

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4

Almendros, Marcos, José Berenguer, and Jose-Vicente Sinisterra. "Thermus thermophilus Nucleoside Phosphorylases Active in the Synthesis of Nucleoside Analogues." Applied and Environmental Microbiology 78, no. 9 (2012): 3128–35. http://dx.doi.org/10.1128/aem.07605-11.

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ABSTRACTCells extracts fromThermus thermophilusHB27 express phosphorolytic activities on purines and pyrimidine nucleosides. Five putative encoding genes were cloned and expressed inEscherichia coli, and the corresponding recombinant proteins were purified and studied. Two of these showed phosphorolytic activities against purine nucleosides, and third one showed phosphorolytic activity against pyrimidine nucleosidesin vitro, and the three were named TtPNPI, TtPNPII, and TtPyNP, respectively. The optimal temperature for the activity of the three enzymes was beyond the water boiling point and co

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5

Kaspar, Felix, Margarita Seeger, Sarah Westarp, et al. "Diversification of 4′-Methylated Nucleosides by Nucleoside Phosphorylases." ACS Catalysis 11, no. 17 (2021): 10830–35. http://dx.doi.org/10.1021/acscatal.1c02589.

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6

Lecoq, K., I. Belloc, C. Desgranges, M. Konrad, and B. Daignan-Fornier. "YLR209c Encodes Saccharomyces cerevisiae Purine Nucleoside Phosphorylase." Journal of Bacteriology 183, no. 16 (2001): 4910–13. http://dx.doi.org/10.1128/jb.183.16.4910-4913.2001.

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ABSTRACT The yeast YLR209c (PNP1) gene encodes a protein highly similar to purine nucleoside phosphorylases. This protein specifically metabolized inosine and guanosine. Disruption ofPNP1 led to inosine and guanosine excretion in the medium, thus showing that PNP1 plays an important role in the metabolism of these purine nucleosides in vivo.

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7

Hormigo, Daniel, Jon Del Arco, Javier Acosta, Maximilian J. L. J. Fürst, and Jesús Fernández-Lucas. "Engineering a Bifunctional Fusion Purine/Pyrimidine Nucleoside Phosphorylase for the Production of Nucleoside Analogs." Biomolecules 14, no. 9 (2024): 1196. http://dx.doi.org/10.3390/biom14091196.

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Nucleoside phosphorylases (NPs) are pivotal enzymes in the salvage pathway, catalyzing the reversible phosphorolysis of nucleosides to produce nucleobases and α-D-ribose 1-phosphate. Due to their efficiency in catalyzing nucleoside synthesis from purine or pyrimidine bases, these enzymes hold significant industrial importance in the production of nucleoside-based drugs. Given that the thermodynamic equilibrium for purine NPs (PNPs) is favorable for nucleoside synthesis—unlike pyrimidine NPs (PyNPs, UP, and TP)—multi-enzymatic systems combining PNPs with PyNPs, UPs, or TPs are commonly employed

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8

Robescu, Marina Simona, Immacolata Serra, Marco Terreni, Daniela Ubiali, and Teodora Bavaro. "A Multi-Enzymatic Cascade Reaction for the Synthesis of Vidarabine 5′-Monophosphate." Catalysts 10, no. 1 (2020): 60. http://dx.doi.org/10.3390/catal10010060.

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We here described a three-step multi-enzymatic reaction for the one-pot synthesis of vidarabine 5′-monophosphate (araA-MP), an antiviral drug, using arabinosyluracil (araU), adenine (Ade), and adenosine triphosphate (ATP) as precursors. To this aim, three enzymes involved in the biosynthesis of nucleosides and nucleotides were used in a cascade mode after immobilization: uridine phosphorylase from Clostridium perfringens (CpUP), a purine nucleoside phosphorylase from Aeromonas hydrophila (AhPNP), and deoxyadenosine kinase from Dictyostelium discoideum (DddAK). Specifically, CpUP catalyzes the

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9

Balaev, Vladislav V., Alexander A. Lashkov, Azat G. Gabdulkhakov, et al. "Structural investigation of the thymidine phosphorylase fromSalmonella typhimuriumin the unliganded state and its complexes with thymidine and uridine." Acta Crystallographica Section F Structural Biology Communications 72, no. 3 (2016): 224–33. http://dx.doi.org/10.1107/s2053230x1600162x.

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Highly specific thymidine phosphorylases catalyze the phosphorolytic cleavage of thymidine, with the help of a phosphate ion, resulting in thymine and 2-deoxy-α-D-ribose 1-phosphate. Thymidine phosphorylases do not catalyze the phosphorolysis of uridine, in contrast to nonspecific pyrimidine nucleoside phosphorylases and uridine phosphorylases. Understanding the mechanism of substrate specificity on the basis of the nucleoside is essential to support rational drug-discovery investigations of new antitumour and anti-infective drugs which are metabolized by thymidine phosphorylases. For this rea

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10

Khandazhinskaya, Anastasia, Barbara Eletskaya, Ilja Fateev, et al. "Novel fleximer pyrazole-containing adenosine analogues: chemical, enzymatic and highly efficient biotechnological synthesis." Organic & Biomolecular Chemistry 19, no. 34 (2021): 7379–89. http://dx.doi.org/10.1039/d1ob01069g.

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11

Zhou, Xinrui, Kathleen Szeker, Lin-Yu Jiao, Martin Oestreich, Igor A. Mikhailopulo, and Peter Neubauer. "Synthesis of 2,6-Dihalogenated Purine Nucleosides by Thermostable Nucleoside Phosphorylases." Advanced Synthesis & Catalysis 357, no. 6 (2015): 1237–44. http://dx.doi.org/10.1002/adsc.201400966.

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12

Mitterbauer, Rudolf, Thomas Karl, and Gerhard Adam. "Saccharomyces cerevisiae URH1 (Encoding Uridine-Cytidine N-Ribohydrolase): Functional Complementation by a Nucleoside Hydrolase from a Protozoan Parasite and by a Mammalian Uridine Phosphorylase." Applied and Environmental Microbiology 68, no. 3 (2002): 1336–43. http://dx.doi.org/10.1128/aem.68.3.1336-1343.2002.

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ABSTRACT Nucleoside hydrolases catalyze the cleavage of N-glycosidic bonds in nucleosides, yielding ribose and the respective bases. While nucleoside hydrolase activity has not been detected in mammalian cells, many protozoan parasites rely on nucleoside hydrolase activity for salvage of purines and/or pyrimidines from their hosts. In contrast, uridine phosphorylase is the key enzyme of pyrimidine salvage in mammalian hosts and many other organisms. We show here that the open reading frame (ORF) YDR400w of Saccharomyces cerevisiae carries the gene encoding uridine hydrolase (URH1). Disruption

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13

VERRI, Annalisa, Federico FOCHER, Richard J. DUNCOMBE, et al. "Anti-(herpes simplex virus) activity of 4′-thio-2′-deoxyuridines: a biochemical investigation for viral and cellular target enzymes." Biochemical Journal 351, no. 2 (2000): 319–26. http://dx.doi.org/10.1042/bj3510319.

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The antiviral activity of several nucleoside analogues is often limited by their rapid degradation by pyrimidine nucleoside phosphorylases. In an attempt to avoid this degradation, several modified nucleosides have been synthesized. A series of 4´-thio-2´-deoxyuridines exhibits an anti-[herpes simplex virus (HSV)] activity significantly higher (20–600 times) than that shown by the corresponding 4´-oxy counterpart. We investigated the mode of action of these compounds and we found that: (i) several 4´-thio-2´-deoxyuridines are phosphorylated to the mono- and di-phosphates by HSV-1 thymidine kin

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14

Drenichev, M. S., E. O. Dorinova, I. V. Varizhuk, et al. "Synthesis of Fluorine-Containing Analogues of Purine Deoxynucleosides: Optimization of Enzymatic Transglycosylation Conditions." Doklady Biochemistry and Biophysics 503, no. 1 (2022): 52–58. http://dx.doi.org/10.1134/s1607672922020053.

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Abstract In this work, a comparative analysis of the conditions of transglycosylation reactions catalyzed by E. coli nucleoside phosphorylases was carried out, and the optimal conditions for the formation of various nucleosides were determined. Under the optimized conditions of transglycosylation reaction, fluorine-containing derivatives of N6-benzyl-2'-deoxyadenosine, potential inhibitors of replication of enteroviruses in a cell, were obtained starting from the corresponding ribonucleosides.

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15

Gomaz, Boris, and Zoran Štefanić. "Oligomeric Symmetry of Purine Nucleoside Phosphorylases." Symmetry 16, no. 1 (2024): 124. http://dx.doi.org/10.3390/sym16010124.

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Many enzymes are composed of several identical subunits, which are arranged in a regular fashion and usually comply with some definite symmetry. This symmetry may be approximate or exact and may or may not coincide with the symmetry of crystallographic packing. Purine nucleoside phosphorylases (PNP) are a class of oligomeric enzymes that show an interesting interplay between their internal symmetry and the symmetry of their crystal packings. There are two main classes of this enzyme: trimeric PNPs, or “low-molecular-mass” proteins, which are found mostly in eukaryotic organisms, and hexameric

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16

Grebenkina, L. E., A. N. Prutkov, A. V. Matveev, and M. V. Chudinov. "Synthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamides." Fine Chemical Technologies 17, no. 4 (2022): 311–22. http://dx.doi.org/10.32362/2410-6593-2022-17-4-311-322.

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Objectives. A key step in the synthesis of natural nucleoside analogs is the formation of a glycosidic bond between the carbohydrate fragment and the heterocyclic base. Glycosylation methods differ in terms of regio- and stereoselectivity. A promising method for the highly specific synthesis of new pharmacologically active compounds involves an enzymatic reaction catalyzed by genetically engineered nucleoside phosphorylases. This study is devoted to the synthesis of a library of analogs of nucleoside heterocyclic bases—5-oxymethyl-1,2,4-triazole- 3-carboxamides—in order to investigate the subs

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17

Yehia, Heba, Sarah Westarp, Viola Röhrs, et al. "Efficient Biocatalytic Synthesis of Dihalogenated Purine Nucleoside Analogues Applying Thermodynamic Calculations." Molecules 25, no. 4 (2020): 934. http://dx.doi.org/10.3390/molecules25040934.

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The enzymatic synthesis of nucleoside analogues has been shown to be a sustainable and efficient alternative to chemical synthesis routes. In this study, dihalogenated nucleoside analogues were produced by thermostable nucleoside phosphorylases in transglycosylation reactions using uridine or thymidine as sugar donors. Prior to the enzymatic process, ideal maximum product yields were calculated after the determination of equilibrium constants through monitoring the equilibrium conversion in analytical-scale reactions. Equilibrium constants for dihalogenated nucleosides were comparable to known

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18

Zhang, Yang, Sarah E. Cottet, and Steven E. Ealick. "Structure of Escherichia coli AMP Nucleosidase Reveals Similarity to Nucleoside Phosphorylases." Structure 12, no. 8 (2004): 1383–94. http://dx.doi.org/10.1016/j.str.2004.05.015.

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19

Liu, Gaofei, Tiantong Cheng, Jianlin Chu, Sui Li, and Bingfang He. "Efficient Synthesis of Purine Nucleoside Analogs by a New Trimeric Purine Nucleoside Phosphorylase from Aneurinibacillus migulanus AM007." Molecules 25, no. 1 (2019): 100. http://dx.doi.org/10.3390/molecules25010100.

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Purine nucleoside phosphorylases (PNPs) are promising biocatalysts for the synthesis of purine nucleoside analogs. Although a number of PNPs have been reported, the development of highly efficient enzymes for industrial applications is still in high demand. Herein, a new trimeric purine nucleoside phosphorylase (AmPNP) from Aneurinibacillus migulanus AM007 was cloned and heterologously expressed in Escherichia coli BL21(DE3). The AmPNP showed good thermostability and a broad range of pH stability. The enzyme was thermostable below 55 °C for 12 h (retaining nearly 100% of its initial activity),

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20

Stepchenko, Vladimir A., Anatoly I. Miroshnikov, Frank Seela, and Igor A. Mikhailopulo. "Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases." Beilstein Journal of Organic Chemistry 12 (December 1, 2016): 2588–601. http://dx.doi.org/10.3762/bjoc.12.254.

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The trans-2-deoxyribosylation of 4-thiouracil (4SUra) and 2-thiouracil (2SUra), as well as 6-azauracil, 6-azathymine and 6-aza-2-thiothymine was studied using dG and E. coli purine nucleoside phosphorylase (PNP) for the in situ generation of 2-deoxy-α-D-ribofuranose-1-phosphate (dRib-1P) followed by its coupling with the bases catalyzed by either E. coli thymidine (TP) or uridine (UP) phosphorylases. 4SUra revealed satisfactory substrate activity for UP and, unexpectedly, complete inertness for TP; no formation of 2’-deoxy-2-thiouridine (2SUd) was observed under analogous reaction conditions i

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21

Tran, Timothy H., S. Christoffersen, Paula W. Allan, et al. "The Crystal Structure ofStreptococcus pyogenesUridine Phosphorylase Reveals a Distinct Subfamily of Nucleoside Phosphorylases." Biochemistry 50, no. 30 (2011): 6549–58. http://dx.doi.org/10.1021/bi200707z.

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22

Eletskaya, Barbara Z., Maria Ya Berzina, Ilya V. Fateev, et al. "Enzymatic Synthesis of 2-Chloropurine Arabinonucleosides with Chiral Amino Acid Amides at the C6 Position and an Evaluation of Antiproliferative Activity In Vitro." International Journal of Molecular Sciences 24, no. 7 (2023): 6223. http://dx.doi.org/10.3390/ijms24076223.

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A number of purine arabinosides containing chiral amino acid amides at the C6 position of the purine were synthesized using a transglycosylation reaction with recombinant E. coli nucleoside phosphorylases. Arsenolysis of 2-chloropurine ribosides with chiral amino acid amides at C6 was used for the enzymatic synthesis, and the reaction equilibrium shifted towards the synthesis of arabinonucleosides. The synthesized nucleosides were shown to be resistant to the action of E. coli adenosine deaminase. The antiproliferative activity of the synthesized nucleosides was studied on human acute myeloid

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23

Antipov, Alexey N., Natalya A. Okorokova, Tatyana N. Safonova, and Vladimir P. Veiko. "Vanadate as a new substrate for nucleoside phosphorylases." JBIC Journal of Biological Inorganic Chemistry 27, no. 2 (2022): 221–27. http://dx.doi.org/10.1007/s00775-021-01923-2.

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24

Lewandowicz, Andrzej, and Vern L. Schramm. "Transition State Analysis for Human andPlasmodiumfalciparumPurine Nucleoside Phosphorylases†." Biochemistry 43, no. 6 (2004): 1458–68. http://dx.doi.org/10.1021/bi0359123.

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25

Bzowska, Agnieszka, Ewa Kulikowska, and David Shugar. "Purine nucleoside phosphorylases: properties, functions, and clinical aspects." Pharmacology & Therapeutics 88, no. 3 (2000): 349–425. http://dx.doi.org/10.1016/s0163-7258(00)00097-8.

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26

Kamel, Sarah, Isabel Thiele, Peter Neubauer, and Anke Wagner. "Thermophilic nucleoside phosphorylases: Their properties, characteristics and applications." Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 1868, no. 2 (2020): 140304. http://dx.doi.org/10.1016/j.bbapap.2019.140304.

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27

Vande Voorde, Johan, Federico Gago, Kristof Vrancken, Sandra Liekens, and Jan Balzarini. "Characterization of pyrimidine nucleoside phosphorylase of Mycoplasma hyorhinis: implications for the clinical efficacy of nucleoside analogues." Biochemical Journal 445, no. 1 (2012): 113–23. http://dx.doi.org/10.1042/bj20112225.

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In the present paper we demonstrate that the cytostatic and antiviral activity of pyrimidine nucleoside analogues is markedly decreased by a Mycoplasma hyorhinis infection and show that the phosphorolytic activity of the mycoplasmas is responsible for this. Since mycoplasmas are (i) an important cause of secondary infections in immunocompromised (e.g. HIV infected) patients and (ii) known to preferentially colonize tumour tissue in cancer patients, catabolic mycoplasma enzymes may compromise efficient chemotherapy of virus infections and cancer. In the genome of M. hyorhinis, a TP (thymidine p

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28

Serra, I., D. Ubiali, A. M. Albertini, G. Amati, S. Daly, and M. Terreni. "Microbial nucleoside phosphorylases as efficient biocatalysts for the synthesis of antiviral and antitumoral nucleosides." Journal of Biotechnology 150 (November 2010): 408. http://dx.doi.org/10.1016/j.jbiotec.2010.09.545.

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29

Zhou, Xinrui, Weizhu Yan, Chong Zhang, et al. "Biocatalytic synthesis of seleno-, thio- and chloro-nucleobase modified nucleosides by thermostable nucleoside phosphorylases." Catalysis Communications 121 (March 2019): 32–37. http://dx.doi.org/10.1016/j.catcom.2018.12.004.

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30

PUGMIRE, Matthew J., and Steven E. EALICK. "Structural analyses reveal two distinct families of nucleoside phosphorylases." Biochemical Journal 361, no. 1 (2002): 1. http://dx.doi.org/10.1042/0264-6021:3610001.

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31

Mordkovich, N. N., A. N. Antipov, N. A. Okorokova, T. N. Safonova, K. M. Polyakov, and V. P. Veiko. "The Nature of Thermal Stability of Prokaryotic Nucleoside Phosphorylases." Applied Biochemistry and Microbiology 56, no. 6 (2020): 662–70. http://dx.doi.org/10.1134/s0003683820060125.

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32

Szeker, K., M. Casteleijn, and P. Neubauer. "Optimization of soluble expression of recombinant thermophilic nucleoside phosphorylases." Journal of Biotechnology 150 (November 2010): 399. http://dx.doi.org/10.1016/j.jbiotec.2010.09.520.

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33

Trembacz, H., and M. M. Jezewska. "Adenine nucleoside phosphorylases in F. hepatica, the mammalian parasite." Clinical Biochemistry 30, no. 3 (1997): 262. http://dx.doi.org/10.1016/s0009-9120(97)87712-0.

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34

Taylor Ringia, Erika A., Peter C. Tyler, Gary B. Evans, Richard H. Furneaux, Andrew S. Murkin, and Vern L. Schramm. "Transition State Analogue Discrimination by Related Purine Nucleoside Phosphorylases." Journal of the American Chemical Society 128, no. 22 (2006): 7126–27. http://dx.doi.org/10.1021/ja061403n.

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35

Ge, Chong-Tao, Li-ming Ouyang, Qing-bao Ding, Li Tan, and Ling Ou. "Expression of recombinant nucleoside phosphorylases and the application in enzymatic synthesis of nucleoside drugs." Journal of Biotechnology 136 (October 2008): S308—S309. http://dx.doi.org/10.1016/j.jbiotec.2008.07.1902.

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36

Timofeev, Vladimir, Yulia Abramchik, Nadezda Zhukhlistova, et al. "3′-Azidothymidine in the active site ofEscherichia colithymidine phosphorylase: the peculiarity of the binding on the basis of X-ray study." Acta Crystallographica Section D Biological Crystallography 70, no. 4 (2014): 1155–65. http://dx.doi.org/10.1107/s1399004714001904.

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The structural study of complexes of thymidine phosphorylase (TP) with nucleoside analogues which inhibit its activity is of special interest because many of these compounds are used as chemotherapeutic agents. Determination of kinetic parameters showed that 3′-azido-3′-deoxythymidine (3′-azidothymidine; AZT), which is widely used for the treatment of human immunodeficiency virus, is a reversible noncompetitive inhibitor ofEscherichia colithymidine phosphorylase (TP). The three-dimensional structure ofE. coliTP complexed with AZT was solved by the molecular-replacement method and was refined a

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37

Zhou, Xinrui, Kathleen Szeker, Bernd Janocha, et al. "Recombinant purine nucleoside phosphorylases from thermophiles: preparation, properties and activity towards purine and pyrimidine nucleosides." FEBS Journal 280, no. 6 (2013): 1475–90. http://dx.doi.org/10.1111/febs.12143.

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38

Pérignon, Jean-Louis, Dominique M. Bories, Anne-Marie Houllier, Laure Thuillier, and Pierre H. Cartier. "Metabolism of pyrimidine bases and nucleosides by pyrimidine-nucleoside phosphorylases in cultured human lymphoid cells." Biochimica et Biophysica Acta (BBA) - Molecular Cell Research 928, no. 2 (1987): 130–36. http://dx.doi.org/10.1016/0167-4889(87)90113-3.

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39

Chae, Whi-Gun, Thomas C. K. Chan, and Ching-jer Chang. "Facile synthesis of 5′-deoxy- and 2′,5′-dideoxy-6-thiopurine nucleosides by nucleoside phosphorylases." Tetrahedron 54, no. 30 (1998): 8661–70. http://dx.doi.org/10.1016/s0040-4020(98)00476-1.

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40

Taran, S. A., K. N. Verevkina, S. A. Feofanov, and A. I. Miroshnikov. "Enzymatic transglycosylation of natural and modified nucleosides by immobilized thermostable nucleoside phosphorylases from Geobacillus stearothermophilus." Russian Journal of Bioorganic Chemistry 35, no. 6 (2009): 739–45. http://dx.doi.org/10.1134/s1068162009060107.

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41

Bychek, Irina A., Anastasia A. Zenchenko, Maria A. Kostromina, et al. "Bacterial Purine Nucleoside Phosphorylases from Mesophilic and Thermophilic Sources: Characterization of Their Interaction with Natural Nucleosides and Modified Arabinofuranoside Analogues." Biomolecules 14, no. 9 (2024): 1069. http://dx.doi.org/10.3390/biom14091069.

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The enzymatic synthesis of nucleoside derivatives is an important alternative to multi-step chemical methods traditionally used for this purpose. Despite several undeniable advantages of the enzymatic approach, there are a number of factors limiting its application, such as the limited substrate specificity of enzymes, the need to work at fairly low concentrations, and the physicochemical properties of substrates—for example, low solubility. This research conducted by our group is dedicated to the advantages and limitations of using purine nucleoside phosphorylases (PNPs), the main enzymes for

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42

Stachelska-Wierzchowska, Wierzchowski, Górka, Bzowska, and Wielgus-Kutrowska. "Tri-Cyclic Nucleobase Analogs and their Ribosides as Substrates of Purine-Nucleoside Phosphorylases. II Guanine and Isoguanine Derivatives." Molecules 24, no. 8 (2019): 1493. http://dx.doi.org/10.3390/molecules24081493.

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Etheno-derivatives of guanine, O6-methylguanine, and isoguanine were prepared and purified using standard methods. The title compounds were examined as potential substrates of purine-nucleoside phosphorylases from various sources in the reverse (synthetic) pathway. It was found that 1,N2-etheno-guanine and 1,N6-etheno-isoguanine are excellent substrates for purine-nucleoside phosphorylase (PNP) from E. coli, while O6-methyl-N2,3-etheno-guanine exhibited moderate activity vs. this enzyme. The latter two compounds displayed intense fluorescence in neutral aqueous medium, and so did the correspon

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43

Christoffersen, S., I. Serra, M. Terreni, and J. Piškur. "Nucleoside Phosphorylases fromClostridium Perfringensin the Synthesis of 2′,3′-Dideoxyinosine." Nucleosides, Nucleotides and Nucleic Acids 29, no. 4-6 (2010): 445–48. http://dx.doi.org/10.1080/15257771003741422.

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44

Chaikuad, Apirat, and R. Leo Brady. "Conservation of structure and activity in Plasmodium purine nucleoside phosphorylases." BMC Structural Biology 9, no. 1 (2009): 42. http://dx.doi.org/10.1186/1472-6807-9-42.

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45

Tomoike, Fumiaki, Seiki Kuramitsu, and Ryoji Masui. "Unique substrate specificity of purine nucleoside phosphorylases from Thermus thermophilus." Extremophiles 17, no. 3 (2013): 505–14. http://dx.doi.org/10.1007/s00792-013-0535-7.

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46

Drenichev, Mikhail S., Vladimir E. Oslovsky, Anastasia A. Zenchenko, et al. "Comparative Analysis of Enzymatic Transglycosylation Using E. coli Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from Ribonucleosides." International Journal of Molecular Sciences 23, no. 5 (2022): 2795. http://dx.doi.org/10.3390/ijms23052795.

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A comparative analysis of the transglycosylation conditions catalyzed by E. coli nucleoside phosphorylases, leading to the formation of 2′-deoxynucleosides, was performed. We demonstrated that maximal yields of 2′-deoxynucleosides, especially modified, can be achieved under small excess of glycosyl-donor (7-methyl-2′-deoxyguanosine, thymidine) and a 4-fold lack of phosphate. A phosphate concentration less than equimolar one allows using only a slight excess of the carbohydrate residue donor nucleoside to increase the reaction’s output. A three-step methodology was elaborated for the preparativ

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Čížková, Zdeňka, Vladimír Maťha, and Karel Beneš. "Enzymatic Synthesis and Its Use in Cladribine Production." Chemické listy 118, no. 12 (2024): 645–49. https://doi.org/10.54779/chl20240645.

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Enzymatic synthesis is an alternative to chemical synthesis and provides new possibilities in the preparation of pharmaceutically active substances. The aim is to minimize the inefficiency of the chemical method of preparation and increase its effectiveness. Despite advances, biotechnological processes in nucleoside synthesis using catalysis by nucleoside phosphorylases are not actively applied industrially. The development of an enzymatic synthesis route could bring benefits in terms of improved efficiency, process simplicity, and minimization of organic solvent consumption and thus environme

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Serra, Immacolata, Simona Daly, Andres R. Alcantara, Davide Bianchi, Marco Terreni, and Daniela Ubiali. "Redesigning the synthesis of vidarabine via a multienzymatic reaction catalyzed by immobilized nucleoside phosphorylases." RSC Advances 5, no. 30 (2015): 23569–77. http://dx.doi.org/10.1039/c4ra15018j.

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The comparison between the biocatalyzed synthesis of araA here described and the chemical synthesis of this nucleoside showed that the enzymatic route is superior (less steps, milder conditions and reagents, easier downstream, lower E-factor).

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Lee, Jeffrey E., Kenneth A. Cornell, Michael K. Riscoe, and P. Lynne Howell. "Structure of E. coli 5′-methylthioadenosine/S-adenosylhomocysteine Nucleosidase Reveals Similarity to the Purine Nucleoside Phosphorylases." Structure 9, no. 10 (2001): 941–53. http://dx.doi.org/10.1016/s0969-2126(01)00656-6.

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Yokomatsu, Tsutomu, Yoshinobu Hayakawa, Taro Kihara, et al. "Synthesis and evaluation of multisubstrate analogue inhibitors of purine nucleoside phosphorylases." Bioorganic & Medicinal Chemistry 8, no. 11 (2000): 2571–79. http://dx.doi.org/10.1016/s0968-0896(00)00192-9.

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