{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,24]],"date-time":"2026-08-24T23:31:25Z","timestamp":1787614285176,"version":"build-2736575974"},"reference-count":46,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2025,6,23]],"date-time":"2025-06-23T00:00:00Z","timestamp":1750636800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["24-14-00458"],"award-info":[{"award-number":["24-14-00458"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>A series of new 3\u2032-deoxyribosides of substituted benzimidazoles was obtained by the chemo-enzymatic method using genetically engineered E. coli purine nucleoside phosphorylase (PNP). In the case of asymmetrically substituted benzimidazole derivatives, a mixture of N1- and N3-regioisomers was formed (confirmed by NMR). The antiviral activity of the obtained compounds against herpes simplex virus 1 of reference strain L2 and a strain deeply resistant to acyclovir in Vero E6 cell culture was studied. 4,6-Difluoro-1-(\u03b2-D-3\u2032-deoxyribofuranosyl)benzimidazole (IC50 = 250.92 \u00b5M, SI = 12.00) and 4,5,6-trifluoro-1-(\u03b2-D-3\u2032-deoxyribofuranosyl)benzimidazole (IC50 = 249.96 \u00b5M, SI = 16.00) showed significant selective activity against both viral models in comparison to ribavirin (IC50 = 511.88 \u00b5M, SI &gt; 8.00).<\/jats:p>","DOI":"10.3390\/biom15070922","type":"journal-article","created":{"date-parts":[[2025,6,24]],"date-time":"2025-06-24T10:44:41Z","timestamp":1750761881000},"page":"922","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["New Benzimidazole 3\u2032-Deoxynucleosides: Synthesis and Antiherpes Virus Properties"],"prefix":"10.3390","volume":"15","author":[{"given":"Aleksandra O.","family":"Arnautova","sequence":"first","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"},{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova St. 32, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irina A.","family":"Aleksakhina","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ekaterina A.","family":"Zorina","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5684-8188","authenticated-orcid":false,"given":"Maria Ya.","family":"Berzina","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8571-4197","authenticated-orcid":false,"given":"Ilya V.","family":"Fateev","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9552-7141","authenticated-orcid":false,"given":"Barbara Z.","family":"Eletskaya","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Konstantin V.","family":"Antonov","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olga S.","family":"Smirnova","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3614-560X","authenticated-orcid":false,"given":"Alexander S.","family":"Paramonov","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3413-0180","authenticated-orcid":false,"given":"Alexey L.","family":"Kayushin","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Valeria L.","family":"Andronova","sequence":"additional","affiliation":[{"name":"Ivanovsky Institute of Virology, Gamaleya National Research Center for Epidemiology, Ministry of Healthcare of the Russian Federation, Gamaleya St. 18, 123098 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Georgii A.","family":"Galegov","sequence":"additional","affiliation":[{"name":"Ivanovsky Institute of Virology, Gamaleya National Research Center for Epidemiology, Ministry of Healthcare of the Russian Federation, Gamaleya St. 18, 123098 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria A.","family":"Kostromina","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9794-7385","authenticated-orcid":false,"given":"Evgeny A.","family":"Zayats","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9849-0447","authenticated-orcid":false,"given":"Inna L.","family":"Karpenko","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova St. 32, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Svetlana K.","family":"Kotovskaya","sequence":"additional","affiliation":[{"name":"Postovsky Institute of Organic Synthesis, The Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya\/Academicheskaya St. 22\/20, 620041 Ekaterinburg, Russia"},{"name":"Department of Organic and Biomolecular Chemistry, Yeltsin Ural Federal University, N., Mira St. 19, 620002 Ekaterinburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9140-358X","authenticated-orcid":false,"given":"Valery N.","family":"Charushin","sequence":"additional","affiliation":[{"name":"Postovsky Institute of Organic Synthesis, The Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya\/Academicheskaya St. 22\/20, 620041 Ekaterinburg, Russia"},{"name":"Department of Organic and Biomolecular Chemistry, Yeltsin Ural Federal University, N., Mira St. 19, 620002 Ekaterinburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3231-5838","authenticated-orcid":false,"given":"Roman S.","family":"Esipov","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anatoly I.","family":"Miroshnikov","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irina D.","family":"Konstantinova","sequence":"additional","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,6,23]]},"reference":[{"key":"ref_1","unstructured":"(2023, April 05). Herpes Simplex Virus. Available online: https:\/\/www.who.int\/ru\/news-room\/fact-sheets\/detail\/herpes-simplex-virus."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1016\/j.jaad.2007.06.027","article-title":"Human herpes simplex virus infections: Epidemiology, pathogenesis, symptomatology, diagnosis, and management","volume":"57","author":"Fatahzadeh","year":"2007","journal-title":"J. Am. Acad. Dermatol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1016\/j.antiviral.2003.09.006","article-title":"Treatment of herpes simplex virus infections","volume":"61","author":"Brady","year":"2004","journal-title":"Antivir. Res."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Sadowski, L.A., Upadhyay, R., Greeley, Z.W., and Margulies, B.J. (2021). Current Drugs to Treat Infections with Herpes Simplex Viruses-1 and -2. Viruses, 13.","DOI":"10.3390\/v13071228"},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Schalkwijk, H.H., Snoeck, R., and Andrei, G. (2022). Acyclovir resistance in herpes simplex viruses: Prevalence and therapeutic alternatives. Biochem. Pharmacol., 206.","DOI":"10.1016\/j.bcp.2022.115322"},{"key":"ref_6","first-page":"14","article-title":"Synthesis, Characterization and Antibacterial Activity of Benzimidazole Derivatives","volume":"4","author":"Sherif","year":"2021","journal-title":"Saudi J. Humanit. Soc. Sci."},{"key":"ref_7","first-page":"100","article-title":"Synthesis and evaluation of antimicrobial, antitubercular and anticancer activities of benzimidazole derivatives","volume":"5","author":"Yadav","year":"2018","journal-title":"Egypt. J. Basic App. Sci."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.compbiolchem.2018.05.021","article-title":"Synthesis, antibacterial activity, synergistic effect, cytotoxicity, docking and molecular dynamics of benzimidazole analogues","volume":"76","author":"Srivastava","year":"2018","journal-title":"Comp. Biol. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1157","DOI":"10.1517\/13543776.2013.800857","article-title":"New substituted benzimidazole derivatives: A patent review (2010\u20132012)","volume":"23","author":"Fei","year":"2014","journal-title":"Expert Opin. Ther. Pat."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"284","DOI":"10.1016\/S1473-3099(11)70024-X","article-title":"Maribavir prophylaxis for prevention of cytomegalovirus disease in recipients of allogeneic stem-cell transplants: A phase 3, double-blind, placebo-controlled, randomised trial","volume":"11","author":"Marty","year":"2011","journal-title":"Lancet Infect. Dis."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2442","DOI":"10.1128\/AAC.01523-10","article-title":"Benzimidazole analogs inhibit human herpesvirus 6","volume":"55","author":"Prichard","year":"2011","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"154","DOI":"10.1016\/j.antiviral.2006.05.002","article-title":"Antiviral drugs for cytomegalovirus diseases","volume":"71","author":"Biron","year":"2006","journal-title":"Antivir. Res."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0065-3527(09)73001-5","article-title":"Looking back in 2009 at the dawning of antiviral therapy now 50 years ago an historical perspective","volume":"73","year":"2009","journal-title":"Adv. Virus Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"227","DOI":"10.1084\/jem.99.3.227","article-title":"Inhibition of influenza virus multiplication by N-glycosides of benzimidazoles-N","volume":"99","author":"Tamm","year":"1954","journal-title":"J. Exp. Med."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/S0065-3527(08)60775-7","article-title":"Halobenzimidazole ribosides and RNA synthesis of cells and viruses","volume":"22","author":"Tamm","year":"1978","journal-title":"Adv. Virus Res."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/0042-6822(57)90032-6","article-title":"Relationship between structure of benzimidazole derivatives and inhibitory activity on vaccinia virus multiplication","volume":"3","author":"Tamm","year":"1957","journal-title":"Virology"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1099\/0022-1317-55-1-87","article-title":"The inhibition of vaccinia virus replication by 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole (DRB): An effect at the assembly stage","volume":"55","author":"Pothier","year":"1981","journal-title":"J. Gen. Virol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1099\/0022-1317-1-1-89","article-title":"The effects of substituted benzimidazoles on the growth of viruses and the nucleic acid metabolism of host cells","volume":"1","author":"Bucknall","year":"1967","journal-title":"J. Gen. Virol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4098","DOI":"10.1021\/jm00020a025","article-title":"Design, synthesis, and antiviral activity of certain 2,5,6-trihalo-1-(beta-D-ribofuranosyl)benzimidazoles","volume":"38","author":"Townsend","year":"1995","journal-title":"J. Med. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1603","DOI":"10.1016\/j.transproceed.2013.01.082","article-title":"Maribavir use in practice for cytomegalovirus infection in French transplantation centers","volume":"45","author":"Alain","year":"2013","journal-title":"Transpl. Proc."},{"key":"ref_21","unstructured":"(2021, December 08). Takeda Announces Publication of Data from SOLSTICE, a Pivotal Phase 3 Trial for LIVTENCITY\u2122 (Maribavir) in Post-Transplant Recipients with Cytomegalovirus (CMV) Infection (Refractory, With or Without Resistance). Available online: https:\/\/www.takeda.com\/newsroom\/newsreleases\/2021\/publication-of-data-from-solstice\/."},{"key":"ref_22","unstructured":"Livtencity (Maribavir) (2022, November 09). An Overview of Livtencity and Why It Is Authorised in the EU. Available online: https:\/\/www.ema.europa.eu\/en\/documents\/overview\/livtencity-epar-medicine-overview_en.pdf."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1515\/znc-1980-1-207","article-title":"Preparation of 1-\u03b1-D arabinofuranosylbenzimidazole and its 5,6-dichloro derivative, and the direct bromination of benzimidazole nucleosides","volume":"35","author":"Kazimierczuk","year":"1980","journal-title":"Z. Naturforsch."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1185","DOI":"10.1021\/ja01562a041","article-title":"Synthesis and biological properties of certain dichlorobenzimidazole ribosides","volume":"79","author":"Kissman","year":"1957","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1080\/15257770008033000","article-title":"Design, synthesis, and antiviral evaluation of 2-deoxy-D-ribosides of substituted benzimidazoles as potential agents for human cytomegalovirus infections","volume":"19","author":"Zou","year":"2000","journal-title":"Nucleosides Nucleotides Nucleic Acids"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"108178","DOI":"10.1016\/j.carres.2020.108178","article-title":"Synthesis of benzimidazole nucleosides and their anticancer activity","volume":"498","author":"Shinde","year":"2020","journal-title":"Carbohydr. Res."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"12544","DOI":"10.1002\/chem.201101508","article-title":"Developments towards regioselective synthesis of 1,2-disubstituted benzimidazoles","volume":"17","author":"Carvalho","year":"2011","journal-title":"Chemistry"},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Ojima, I. (2009). Fluorine in Medicinal Chemistry and Chemical Biology, Wiley.","DOI":"10.1002\/9781444312096"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1043","DOI":"10.1055\/s-0036-1588625","article-title":"Chemoenzymatic Synthesis of Modified 2\u2032-Deoxy-2\u2032-fluoro-\u03b2-Darabinofuranosyl Benzimidazoles and Evaluation of Their Activity Against Herpes Simplex Virus Type 1","volume":"49","author":"Kharitonova","year":"2017","journal-title":"Synthesis"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"4853","DOI":"10.1055\/s-0036-1590804","article-title":"The Chemoenzymatic Synthesis of 2-Chloro- and 2-Fluorocordycepins","volume":"49","author":"Denisova","year":"2017","journal-title":"Synthesis"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1006\/prep.2001.1524","article-title":"Overexpression of Escherichia coli genes encoding nucleoside phosphorylases in the pET\/Bl21(DE3) system yields active recombinant enzymes","volume":"24","author":"Esipov","year":"2002","journal-title":"Protein Expr. Purif."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1147","DOI":"10.1016\/j.enzmictec.2006.08.022","article-title":"Synthesis of 2\u2032-deoxyibosylnucleosides using new 2\u2032-deoxyribosyltransferase microorganism producers","volume":"40","author":"Condezo","year":"2007","journal-title":"Enzym. Microb. Technol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3773","DOI":"10.1007\/s00253-013-4816-y","article-title":"New insights on nucleoside 2\u2032-deoxyribosyltransferases: A versatile biocatalyst for one-pot one-step synthesis of nucleoside analogs","volume":"97","author":"Arroyo","year":"2013","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"14400","DOI":"10.1074\/jbc.M111995200","article-title":"Functional cloning, heterologous expression, and purification of two different N-deoxyribosyltransferases from Lactobacillus helveticus","volume":"277","author":"Kaminski","year":"2002","journal-title":"J. Biol. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"477","DOI":"10.1080\/15257779508012409","article-title":"Benzimidazoles in The Reaction of Enzymatic Transglycosylation","volume":"14","author":"Mikhailopulo","year":"1995","journal-title":"Nucleosides Nucleotides"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1006\/jmbi.1998.1799","article-title":"Crystal structure of the ternary complex of E. coli purine nucleoside phosphorilase with formycin B a structural analogue of the substrate inosine and phosphate (sulphate) at 2.1 Ao resolution","volume":"280","author":"Koellner","year":"1998","journal-title":"J. Mol. Biol."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1016\/S0163-7258(00)00097-8","article-title":"Purine nucleoside phosphorylases: Properties, functions and clinical aspects","volume":"88","author":"Bzowska","year":"2000","journal-title":"Pharmacol. Ther."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"2484","DOI":"10.1016\/j.bmcl.2017.03.100","article-title":"New modified 2-aminobenzimidazole nucleosides: Synthesis and evaluation of their activity against herpes simplex virus type 1","volume":"27","author":"Kharitonova","year":"2017","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"16325","DOI":"10.1039\/D0CP03062G","article-title":"The multifaceted effects of DMSO and high hydrostatic pressure on the kinetic constants of hydrolysis reactions catalyzed by \u03b1-chymotrypsin","volume":"22","author":"Ostermeier","year":"2020","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"e21774","DOI":"10.1096\/fj.202100994","article-title":"Dimethyl sulfoxide reduces the stability but enhances catalytic activity of the main SARS-CoV-2 protease 3CLpro","volume":"35","author":"Ferreira","year":"2021","journal-title":"FASEB J."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4962","DOI":"10.1016\/j.biortech.2011.01.088","article-title":"Influence of organic co-solvents on the activity and substrate specificity of feruloyl esterases","volume":"102","author":"Faulds","year":"2011","journal-title":"Bioresour. Technol."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"446","DOI":"10.1271\/bbb.63.446","article-title":"Substrate specificity of aqualysin I altered by an organic solvent, DMSO","volume":"63","author":"Tanaka","year":"1999","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1006\/jmbi.2001.5211","article-title":"Open and closed conformation of the E. coli purine nucleoside phosphorylase active center and implications for the catalytic mechanism","volume":"315","author":"Koellner","year":"2002","journal-title":"J. Mol. Biol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"394","DOI":"10.1055\/s-0035-1560911","article-title":"Chemo-Enzymatic Syntheses and Antiviral Evaluation of 5-substituted 4,6-difluorobenzimidazoles Ribo- and 2\u2032-Deoxyribo-Nucleosides","volume":"48","author":"Kharitonova","year":"2016","journal-title":"Synthesis"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"717","DOI":"10.1128\/JVI.72.1.717-725.1998","article-title":"Inhibition of human cytomegalovirus DNA maturation by a benzimidazole ribonucleoside is mediated through the UL89 gene product","volume":"72","author":"Underwood","year":"1998","journal-title":"J. Virol."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"705","DOI":"10.1126\/science.177.4050.705","article-title":"Broad-spectrum antiviral activity of Virazole: 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide","volume":"177","author":"Sidwell","year":"1972","journal-title":"Science"}],"container-title":["Biomolecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2218-273X\/15\/7\/922\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T17:57:20Z","timestamp":1760032640000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2218-273X\/15\/7\/922"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,6,23]]},"references-count":46,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2025,7]]}},"alternative-id":["biom15070922"],"URL":"https:\/\/doi.org\/10.3390\/biom15070922","relation":{},"ISSN":["2218-273X"],"issn-type":[{"value":"2218-273X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,6,23]]}}}