OPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHOD
Disaccharide nucleosides belong to an important group of natural compounds found in t-RNA and poly(ADPribose). They are also key elements in the structure of antibiotics and other physiologically active compounds. Poly(ADP-ribosylation) is a posttranslational modification of proteins in eukariotic c...
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MIREA - Russian Technological University
2013-08-01
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| Series: | Тонкие химические технологии |
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| Online Access: | https://www.finechem-mirea.ru/jour/article/view/566 |
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| author | V. E. Oslovsky M. S. Drenichev S. N. Mikhailov E. Yu. Bulychev |
| author_facet | V. E. Oslovsky M. S. Drenichev S. N. Mikhailov E. Yu. Bulychev |
| author_sort | V. E. Oslovsky |
| collection | DOAJ |
| description | Disaccharide nucleosides belong to an important group of natural compounds found in t-RNA and poly(ADPribose). They are also key elements in the structure of antibiotics and other physiologically active compounds. Poly(ADP-ribosylation) is a posttranslational modification of proteins in eukariotic cells catalyzed by poly(ADPribose)-polymerazes. The importance of poly(ADP-ribose) has been established in many cellular processes such as DNA replication, recombination and repair and cellular differentiation. The development of the synthesis of poly(ADP-ribose) and it’s components is still a challenging problem. The synthesis of 2'-O-α-D-ribofuranosyladenosine, a monomeric unit of poly(ADP-ribose) reported earlier has been improved. An important step on this way is the formation of a 2'-O-glycosidic bond between the adenosine and carbohydrate moieties. A new strategy involving glycosylation of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine has been suggested. Varying of the catalyst (SnCl4), nucleoside and carbohydrate relations by the simplex method allowed improving the yields in the glycosylation step from 35 to 64%. As a result, it made possible to reach a higher overall yield of 2'-O-α-D-ribofuranosyladenosine in comparison with the literature data. |
| format | Article |
| id | doaj-art-1ac078057bcc4601a7697a2fb582d657 |
| institution | Kabale University |
| issn | 2410-6593 2686-7575 |
| language | Russian |
| publishDate | 2013-08-01 |
| publisher | MIREA - Russian Technological University |
| record_format | Article |
| series | Тонкие химические технологии |
| spelling | doaj-art-1ac078057bcc4601a7697a2fb582d6572025-08-20T03:56:23ZrusMIREA - Russian Technological UniversityТонкие химические технологии2410-65932686-75752013-08-01842732560OPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHODV. E. Oslovsky0M. S. Drenichev1S. N. Mikhailov2E. Yu. Bulychev3V.A. Engelhardt Institute of Molecular Biology RAS, Moscow, 119991V.A. Engelhardt Institute of Molecular Biology RAS, Moscow, 119991V.A. Engelhardt Institute of Molecular Biology RAS, Moscow, 119991M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571Disaccharide nucleosides belong to an important group of natural compounds found in t-RNA and poly(ADPribose). They are also key elements in the structure of antibiotics and other physiologically active compounds. Poly(ADP-ribosylation) is a posttranslational modification of proteins in eukariotic cells catalyzed by poly(ADPribose)-polymerazes. The importance of poly(ADP-ribose) has been established in many cellular processes such as DNA replication, recombination and repair and cellular differentiation. The development of the synthesis of poly(ADP-ribose) and it’s components is still a challenging problem. The synthesis of 2'-O-α-D-ribofuranosyladenosine, a monomeric unit of poly(ADP-ribose) reported earlier has been improved. An important step on this way is the formation of a 2'-O-glycosidic bond between the adenosine and carbohydrate moieties. A new strategy involving glycosylation of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine has been suggested. Varying of the catalyst (SnCl4), nucleoside and carbohydrate relations by the simplex method allowed improving the yields in the glycosylation step from 35 to 64%. As a result, it made possible to reach a higher overall yield of 2'-O-α-D-ribofuranosyladenosine in comparison with the literature data.https://www.finechem-mirea.ru/jour/article/view/566disaccharide nucleosides, poly(adp-ribose), glycosylation, optimization. |
| spellingShingle | V. E. Oslovsky M. S. Drenichev S. N. Mikhailov E. Yu. Bulychev OPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHOD Тонкие химические технологии disaccharide nucleosides, poly(adp-ribose), glycosylation, optimization. |
| title | OPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHOD |
| title_full | OPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHOD |
| title_fullStr | OPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHOD |
| title_full_unstemmed | OPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHOD |
| title_short | OPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHOD |
| title_sort | optimization of 2 о α d ribofuranosyladenosine synthesis using the simplex planning method |
| topic | disaccharide nucleosides, poly(adp-ribose), glycosylation, optimization. |
| url | https://www.finechem-mirea.ru/jour/article/view/566 |
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