chemicallytechFine Chemical TechnologiesТонкие химические технологии2410-65932686-7575MIREA – Russian Technological University (RTU MIREA).chemicallytech-566Research ArticleCHEMISTRY AND TECHNOLOGY OF MEDICINAL COMPOUNDS AND BIOLOGICALLY ACTIVE SUBSTANCESХИМИЯ И ТЕХНОЛОГИЯ ЛЕКАРСТВЕННЫХ ПРЕПАРАТОВ И БИОЛОГИЧЕСКИ АКТИВНЫХ СОЕДИНЕНИЙOPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHODОПТИМИЗАЦИЯ СИНТЕЗА 2'- О-α- D-РИБОФУРАНОЗИЛАДЕНОЗИНА ПО МЕТОДУ СИМПЛЕКСНОГО ПЛАНИРОВАНИЯОсловскийВ. Е.OslovskyV. E.

аспирант

vladimiroslovsky@gmail.comДреничевМ. С.DrenichevM. S.

младший научный сотрудник

noemail@neicon.ruМихайловС. Н.MikhailovS. N.

заведующий лабораторией

noemail@neicon.ruБулычевЭ. Ю.BulychevE. Yu.

кафедра Химии и технологии биологически активных соединений им. Н.А. Преображенского, доцент

noemail@neicon.ruИнститут молекулярной биологии им. В.А. Энгельгардта РАН, Москва, 119991РоссияV.A. Engelhardt Institute of Molecular Biology RAS, Moscow, 119991Russian FederationМИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86РоссияM.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571Russian Federation201328082013842732Copyright © Oslovsky V.E., Drenichev M.S., Mikhailov S.N., Bulychev E.Y., 20132013Ословский В.Е., Дреничев М.С., Михайлов С.Н., Булычев Э.Ю.Oslovsky V.E., Drenichev M.S., Mikhailov S.N., Bulychev E.Y.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.finechem-mirea.ru/jour/article/view/566

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.

С помощью метода симплексного планирования оптимизирован синтез 2'-O-α-D-рибофура-нозиладенозина - мономерного звена поли(АDP-рибозы). Подбор оптимальных соотношений катализатора (SnCl4), нуклеозида и углеводной компоненты позволил повысить выходы на стадии гликозилирования с 35 до 64%.

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The authors declare that there are no conflicts of interest present.