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<article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns:ali="http://www.niso.org/schemas/ali/1.0/" article-type="research-article" dtd-version="1.2" xml:lang="en"><front><journal-meta><journal-id journal-id-type="publisher-id">Doklady Biological Sciences</journal-id><journal-title-group><journal-title xml:lang="en">Doklady Biological Sciences</journal-title><trans-title-group xml:lang="ru"><trans-title>Доклады Российской академии наук. Науки о жизни</trans-title></trans-title-group></journal-title-group><issn publication-format="print">2686-7389</issn><issn publication-format="electronic">3034-5057</issn><publisher><publisher-name xml:lang="en">The Russian Academy of Sciences</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="publisher-id">693503</article-id><article-id pub-id-type="doi">10.31857/S2686738925040098</article-id><article-categories><subj-group subj-group-type="toc-heading" xml:lang="en"><subject>Articles</subject></subj-group><subj-group subj-group-type="toc-heading" xml:lang="ru"><subject>Статьи</subject></subj-group><subj-group subj-group-type="article-type"><subject>Research Article</subject></subj-group></article-categories><title-group><article-title xml:lang="en">Preparation of 6-azido-2-chloropurine-2′-deoxyriboside by enzymatic transglycosylation reaction catalyzed by Lactobacillus leichmannii type 2 nucleoside deoxyribosyltransferase</article-title><trans-title-group xml:lang="ru"><trans-title>Получение 6-азидо-2-хлорпурин-2′-дезоксирибозида с помощью реакции ферментативного трансгликозилирования, катализируемой нуклеозиддезоксирибозилтрансферазой второго типа Lactobacillus leichmannii</trans-title></trans-title-group></title-group><contrib-group><contrib contrib-type="author"><name-alternatives><name xml:lang="en"><surname>Alexeev</surname><given-names>C. S.</given-names></name><name xml:lang="ru"><surname>Алексеев</surname><given-names>К. С.</given-names></name></name-alternatives><email>micelle@mail.ru</email><xref ref-type="aff" rid="aff1"/></contrib><contrib contrib-type="author"><name-alternatives><name xml:lang="en"><surname>Konkina</surname><given-names>M. A.</given-names></name><name xml:lang="ru"><surname>Конкина</surname><given-names>М. А.</given-names></name></name-alternatives><email>cyril.alex@eimb.ru</email><xref ref-type="aff" rid="aff1"/><xref ref-type="aff" rid="aff2"/></contrib><contrib contrib-type="author"><name-alternatives><name xml:lang="en"><surname>Kurochkin</surname><given-names>N. N.</given-names></name><name xml:lang="ru"><surname>Курочкин</surname><given-names>Н. Н.</given-names></name></name-alternatives><email>micelle@mail.ru</email><xref ref-type="aff" rid="aff1"/></contrib><contrib contrib-type="author"><name-alternatives><name xml:lang="en"><surname>Drenichev</surname><given-names>M. S.</given-names></name><name xml:lang="ru"><surname>Дреничев</surname><given-names>М. С.</given-names></name></name-alternatives><email>micelle@mail.ru</email><xref ref-type="aff" rid="aff1"/></contrib></contrib-group><aff-alternatives id="aff1"><aff><institution xml:lang="en">Engelhardt Institute of Molecular Biology, Russian Academy of Sciences</institution></aff><aff><institution xml:lang="ru">Институт молекулярной биологии им. В. А. Энгельгардта Российской академии наук</institution></aff></aff-alternatives><aff-alternatives id="aff2"><aff><institution xml:lang="en">Lomonosov Institute of Fine Chemical Technologies, MIREA Russia Technological University</institution></aff><aff><institution xml:lang="ru">Институт тонких химических технологий имени М. В. Ломоносова, “МИРЭА – Российский технологический университет”</institution></aff></aff-alternatives><pub-date date-type="pub" iso-8601-date="2025-08-15" publication-format="electronic"><day>15</day><month>08</month><year>2025</year></pub-date><volume>523</volume><issue>1</issue><issue-title xml:lang="en">VOL 523, NO (2025)</issue-title><issue-title xml:lang="ru">ТОМ 523, № (2025)</issue-title><fpage>431</fpage><lpage>438</lpage><history><date date-type="received" iso-8601-date="2025-10-16"><day>16</day><month>10</month><year>2025</year></date></history><permissions><copyright-statement xml:lang="en">Copyright ©; 2025, Russian Academy of Sciences</copyright-statement><copyright-statement xml:lang="ru">Copyright ©; 2025, Российская академия наук</copyright-statement><copyright-year>2025</copyright-year><copyright-holder xml:lang="en">Russian Academy of Sciences</copyright-holder><copyright-holder xml:lang="ru">Российская академия наук</copyright-holder></permissions><self-uri xlink:href="https://journals.eco-vector.com/2686-7389/article/view/693503">https://journals.eco-vector.com/2686-7389/article/view/693503</self-uri><abstract xml:lang="en"><p>6-azido-2-chloropurine-2′-deoxyriboside, a valuable precursor for the preparation of modified 2-chloropurine nucleosides substituted at the 6-position of the heterocyclic base, was obtained by enzymatic transglycosylation. 6-azido-2-chloropurine-2′-deoxyriboside can also be used as a photocross-linking agent to study the nucleic acids – proteins interactions. A type 2 nucleoside deoxyribosyltransferase from Lactobacillus leichmannii was used as a biocatalyst. The optimal conditions for the formation of 6-azido-2-chloropurine-2′-deoxyriboside using 7-methyl-2′-deoxyguanosine as a carbohydrate residue donor were determined.</p></abstract><trans-abstract xml:lang="ru"><p>6-azido-2-chloropurine-2′-deoxyriboside, a valuable precursor for the preparation of modified 2-chloropurine nucleosides substituted at the 6-position of the heterocyclic base, was obtained by enzymatic transglycosylation. 6-azido-2-chloropurine-2′-deoxyriboside can also be used as a photocross-linking agent to study the nucleic acids – proteins interactions. A type 2 nucleoside deoxyribosyltransferase from Lactobacillus leichmannii was used as a biocatalyst. The optimal conditions for the formation of 6-azido-2-chloropurine-2′-deoxyriboside using 7-methyl-2′-deoxyguanosine as a carbohydrate residue donor were determined.</p></trans-abstract><kwd-group xml:lang="en"><kwd>6-azido-2-chloropurine</kwd><kwd>nucleosides</kwd><kwd>nucleoside deoxyribosyltransferase</kwd><kwd>7-methyl-2′-deoxyguanosine</kwd><kwd>enzymatic transglycosylation</kwd><kwd>modified purine</kwd><kwd>photocross-linking agent</kwd></kwd-group><kwd-group xml:lang="ru"><kwd>6-азидо-2-хлорпурин</kwd><kwd>нуклеозиды</kwd><kwd>нуклеозиддезоксирибозилтрансфераза</kwd><kwd>7-метил-2′-дезоксигуанозин</kwd><kwd>ферментативное трансгликозилирование</kwd><kwd>модифицированный пурин</kwd><kwd>фотокросс-сшивающий агент</kwd></kwd-group><funding-group><funding-statement xml:lang="ru">Работа выполнена при финансовой поддержке Российского Научного Фонда (проект РНФ № 24-24-00542).</funding-statement></funding-group></article-meta></front><body></body><back><ref-list><ref id="B1"><label>1.</label><mixed-citation>Iglesias L.E., Lewkowicz E. S., Medici R., et al. Biocatalytic approaches applied to the synthesis of nucleoside prodrugs // Biotechnol. Adv. 2015, Vol. 33, N5. P. 412–434. DOI: 10.1016/j.biotechadv.2015.03.009</mixed-citation></ref><ref id="B2"><label>2.</label><mixed-citation>Holguin J., Cardinaud R. Trans-N-Deoxyribosylase: Purification by Affinity Chromatography and Characterization // Eur. J. Biochem. 1975. Vol. 54, N2. P. 505–514. PMID: 1175596. https://doi.org/10.1111/j.1432–1033.1975.tb04163.x;</mixed-citation></ref><ref id="B3"><label>3.</label><mixed-citation>Kaminski P. A. Functional Cloning, Heterologous Expression, and Purification of Two Different N-Deoxyribosyltransferases from Lactobacillus helveticus // J. Biol. Chem. 2002. Vol. 277, N17. P. 14400–14407. PMID: 11836245. https://doi.org/10.1074/jbc.M111995200</mixed-citation></ref><ref id="B4"><label>4.</label><mixed-citation>Del Arco J., Perona A., González L., et al. Reaction mechanism of nucleoside 2′-deoxyribosyltransferases: free-energy landscape supports an oxocarbenium ion as the reaction intermediate. // Org. Biomol. Chem. 2019. Vol. 17, N34. P. 7891–7899. https://doi.org/10.1039/c9ob01315f.</mixed-citation></ref><ref id="B5"><label>5.</label><mixed-citation>Becker J., Brendel M. Rapid Purification and Characterization of Two Distinct N-Deoxyribosyltransferases of Lactobacillus leichmannii // Biol. Chem. Hoppe Seyler. 1996. Vol. 377, N6. P. 357–362. PMID: 8839981. https://doi.org/10.1515/bchm3.1996.377.6.357</mixed-citation></ref><ref id="B6"><label>6.</label><mixed-citation>Crespo N, Sánchez-Murcia P. A., Gago F., et. al. 2′-Deoxyribosyltransferase from Leishmania mexicana, an efficient biocatalyst for one-pot, one-step synthesis of nucleosides from poorly soluble purine bases // Appl. Microbiol. Biotechnol. 2017. Vol. 101, N19. P. 7187–7200. PMID: 28785897. https://doi.org/10.1007/s00253-017-8450-y</mixed-citation></ref><ref id="B7"><label>7.</label><mixed-citation>Pérez E., Sánchez-Murcia P. A., Jordaan J., et. al. Enzymatic Synthesis of Therapeutic Nucleosides using a Highly Versatile Purine Nucleoside 2'-DeoxyribosylTransferase from Trypanosoma brucei // Chem. Cat. Chem. 2018. Vol. 10, N19. P. 4406–4416. https://doi.org/10.1002/cctc.201800775</mixed-citation></ref><ref id="B8"><label>8.</label><mixed-citation>Cardinaud R, Holguin J. Nucleoside deoxyribosyltransferase-II from Lactobacillus helveticus. Substrate specificity studies. Pyrimidine bases as acceptors // Biochim. Biophys. Acta – Enzymology. 1979. Vol. 568, N2. P. 339–347. PMID: 486487. https://doi.org/10.1016/0005-2744(79)90301-2</mixed-citation></ref><ref id="B9"><label>9.</label><mixed-citation>Fernández-Lucas J., Acebal C., Sinisterra J. V., et al. Lactobacillus reuteri 2′-Deoxyribosyltransferase, a Novel Biocatalyst for Tailoring of Nucleosides // Appl. Environ. Microbiol. 2010. Vol. 76, N5. P. 1462–1470. PMID: 20048065; PMCID: PMC2832402. https://doi.org/10.1128/AEM.01685-09</mixed-citation></ref><ref id="B10"><label>10.</label><mixed-citation>Del Arco J., Acosta J., Fernández-Lucas J. New trends in the biocatalytic production of nucleosidic active pharmaceutical ingredients using 2′-deoxyribosyltransferases // Biotechnol. Adv. 2021. Vol. 51. P. 107701. PMID: 33515673 https://doi.org 10.1016/ j.biotechadv.2021.107701</mixed-citation></ref><ref id="B11"><label>11.</label><mixed-citation>Kovaļovs A., Novosjolova I, Bizdēna Ē., et al. 1, 2, 3-Triazoles as leaving groups in purine chemistry: a three-step synthesis of N6-substituted-2-triazolyl-adenine nucleosides and photophysical properties thereof //Tetrahedron Letters. 2013. Vol. 54, N8. P. 850–853. https://doi.org/10.1016/j.tetlet.2012.11.095</mixed-citation></ref><ref id="B12"><label>12.</label><mixed-citation>Meisenheimer K. M., Koch T. H. Photocross-Linking of Nucleic Acids to Associated Proteins // Critical Reviews in Biochemistry and Molecular Biology. 1997. Vol. 32, N2. P. 101–140. https://doi.org/10.3109/10409239709108550</mixed-citation></ref><ref id="B13"><label>13.</label><mixed-citation>Salihovic A., Ascham A., Taladriz-Sender A., et al. Gram-scale enzymatic synthesis of 2′-deoxyribonucleoside analogues using nucleoside transglycosylase-2 // Chem. Sci. 2024. Vol. 15. P. 15399–15407. https://doi.org/10.1039/D4SC04938As</mixed-citation></ref><ref id="B14"><label>14.</label><mixed-citation>Konkina M.A., Drenichev M. S., Nasyrova D. I., et al. Studies on enzymatic transglycosylation catalyzed by bacterial Nucleoside deoxyribosyltransferase II and Nucleoside phosphorylase for the synthesis of pyrimidine 2′-Deoxyribonucleosides containing modified heterocyclic base // Sustain. Chem. and Pharm. 2023. Vol. 32. P. 101011. https://doi.org/10.1016/j.scp.2023.101011</mixed-citation></ref><ref id="B15"><label>15.</label><mixed-citation>Frieden M., Aviñó A., Eritja R. Convenient Synthesis of 8-Amino-2′-deoxyadenosine // Nucleosides, Nucleotides &amp; Nucleic Acids. 2003. Vol. 22, N2. P. 193–202. https://doi.org/10.1081/NCN-120019521</mixed-citation></ref><ref id="B16"><label>16.</label><mixed-citation>Lakshman M. K., Singh M. K., Parrish D., et al. Azide– Tetrazole equilibrium of C-6 azidopurine nucleosides and their ligation reactions with alkynes // The Journal of organic chemistry. 2010. Vol. 75, N8. P. 2461–2473.</mixed-citation></ref><ref id="B17"><label>17.</label><mixed-citation>Drenichev M.S., Alexeev C. S., Kurochkin N. N., et al. Use of nucleoside phosphorylases for the preparation of purine and pyrimidine 2′-deoxynucleosides. // Adv. Synth. Catal. 2018. Vol.360. P. 305–312. https://doi.org/10.1002/adsc.201701005.</mixed-citation></ref><ref id="B18"><label>18.</label><mixed-citation>Rabuffetti M., Bavaro, T., Semproli, R., et al. Synthesis of ribavirin, tecadenoson, and cladribine by enzymatic transglycosylation. // Catalysts. 2019. Vol. 9. P. 355. DOI: 10.3390/catal9040355.</mixed-citation></ref><ref id="B19"><label>19.</label><mixed-citation>Komodziński K., Nowak J., Lepczyńska J., et. al. Photochemistry of 6-azidopurine ribonucleoside in aqueous solution // Tetrahedron Lett. 2012. Vol. 53, N18. P. 2316–2318. https://doi.org/10.1016/j.tetlet.2012.02.103.</mixed-citation></ref></ref-list></back></article>
