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OPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHOD

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Abstract

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.

About the Authors

V. E. Oslovsky
V.A. Engelhardt Institute of Molecular Biology RAS, Moscow, 119991
Russian Federation


M. S. Drenichev
V.A. Engelhardt Institute of Molecular Biology RAS, Moscow, 119991
Russian Federation


S. N. Mikhailov
V.A. Engelhardt Institute of Molecular Biology RAS, Moscow, 119991
Russian Federation


E. Yu. Bulychev
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


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For citation:


Oslovsky V.E., Drenichev M.S., Mikhailov S.N., Bulychev E.Yu. OPTIMIZATION OF 2'-О-α-D-RIBOFURANOSYLADENOSINE SYNTHESIS USING THE SIMPLEX PLANNING METHOD. Fine Chemical Technologies. 2013;8(4):27-32. (In Russ.)

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ISSN 2410-6593 (Print)
ISSN 2686-7575 (Online)