Synthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamides
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...
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MIREA - Russian Technological University
2022-09-01
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| Series: | Тонкие химические технологии |
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| Online Access: | https://www.finechem-mirea.ru/jour/article/view/1859 |
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| author | L. E. Grebenkina A. N. Prutkov A. V. Matveev M. V. Chudinov |
| author_facet | L. E. Grebenkina A. N. Prutkov A. V. Matveev M. V. Chudinov |
| author_sort | L. E. Grebenkina |
| collection | DOAJ |
| description | 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 substrate specificity of genetically engineered nucleoside phosphorylases.Methods. A method of cyclization of acylamidrazones obtained from the single synthetic precursor β-N-tert-butyloxycarbonyl-oxalamidrazone was used to parallel-synthesize new 5-alkoxy/ aryloxymethyl-1,2,4-triazole-3-carboxamides. Silica gel column chromatography was used to isolate and purify the synthesized compounds. A complex of physicochemical analysis methods (nuclear magnetic resonance spectroscopy, chromatography, and mass spectrometry) confirmed the structure of the compounds obtained in the work.Results. 5-alkoxy/aryloxymethyl-1,2,4-triazole-3-carboxamides were obtained to study the substrate specificity of genetically engineered nucleoside phosphorylases. The possibility of obtaining new nucleoside analogs by the chemico-enzymatic method was demonstrated on the basis of preliminary assessment results.Conclusions. The physicochemical characteristics of a series of novel 5-alkoxy/aryloxymethyl- 1,2,4-triazole-3-carboxamides were studied along with their potential to act as substrates for the transglycosylation reaction catalyzed by nucleoside phosphorylases. |
| format | Article |
| id | doaj-art-5955fd175ddb48e6a88e8459c8296d11 |
| institution | DOAJ |
| issn | 2410-6593 2686-7575 |
| language | Russian |
| publishDate | 2022-09-01 |
| publisher | MIREA - Russian Technological University |
| record_format | Article |
| series | Тонкие химические технологии |
| spelling | doaj-art-5955fd175ddb48e6a88e8459c8296d112025-08-20T02:59:43ZrusMIREA - Russian Technological UniversityТонкие химические технологии2410-65932686-75752022-09-0117431132210.32362/2410-6593-2022-17-4-311-3221686Synthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamidesL. E. Grebenkina0A. N. Prutkov1A. V. Matveev2M. V. Chudinov3MIREA - Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)MIREA - Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)MIREA - Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)MIREA - Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)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 substrate specificity of genetically engineered nucleoside phosphorylases.Methods. A method of cyclization of acylamidrazones obtained from the single synthetic precursor β-N-tert-butyloxycarbonyl-oxalamidrazone was used to parallel-synthesize new 5-alkoxy/ aryloxymethyl-1,2,4-triazole-3-carboxamides. Silica gel column chromatography was used to isolate and purify the synthesized compounds. A complex of physicochemical analysis methods (nuclear magnetic resonance spectroscopy, chromatography, and mass spectrometry) confirmed the structure of the compounds obtained in the work.Results. 5-alkoxy/aryloxymethyl-1,2,4-triazole-3-carboxamides were obtained to study the substrate specificity of genetically engineered nucleoside phosphorylases. The possibility of obtaining new nucleoside analogs by the chemico-enzymatic method was demonstrated on the basis of preliminary assessment results.Conclusions. The physicochemical characteristics of a series of novel 5-alkoxy/aryloxymethyl- 1,2,4-triazole-3-carboxamides were studied along with their potential to act as substrates for the transglycosylation reaction catalyzed by nucleoside phosphorylases.https://www.finechem-mirea.ru/jour/article/view/1859nucleoside analogs5-oximethyl-1,2,4-triazole-3-carboxamidesparallel synthesisnucleoside phosphorylasesubstrate specificity |
| spellingShingle | L. E. Grebenkina A. N. Prutkov A. V. Matveev M. V. Chudinov Synthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamides Тонкие химические технологии nucleoside analogs 5-oximethyl-1,2,4-triazole-3-carboxamides parallel synthesis nucleoside phosphorylase substrate specificity |
| title | Synthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamides |
| title_full | Synthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamides |
| title_fullStr | Synthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamides |
| title_full_unstemmed | Synthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamides |
| title_short | Synthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamides |
| title_sort | synthesis of 5 oxymethyl 1 2 4 triazole 3 carboxamides |
| topic | nucleoside analogs 5-oximethyl-1,2,4-triazole-3-carboxamides parallel synthesis nucleoside phosphorylase substrate specificity |
| url | https://www.finechem-mirea.ru/jour/article/view/1859 |
| work_keys_str_mv | AT legrebenkina synthesisof5oxymethyl124triazole3carboxamides AT anprutkov synthesisof5oxymethyl124triazole3carboxamides AT avmatveev synthesisof5oxymethyl124triazole3carboxamides AT mvchudinov synthesisof5oxymethyl124triazole3carboxamides |