Organizing co mmittee

CHEMICAL SYNTHESIS OF 2-AMINOBENZIMIDAZOLE 
3’-DEOXYRIBOSIDE 
 
Zorina E.A.
1,2
, Kayushin A.L.
2
, Arnautova A.O.
2
, Konstantinova I.D.
2 
 
1
MIREA – Russian Technological University, 86 Vernadsky Avenue, Moscow, 
119571, Russia 
2
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS, Miklukho-
Maklaya 16/10, 117997 GSP, B-437 Moscow, Russia 
 
Nucleoside analogues are used in medical practice due to their wide range of activity. 
They are used in treatment of viral diseases, malignant neoplasms, parasitic diseases, as 
well as bacterial and fungal infections. Different derivatives of benzimidazole 
nucleosides are known to be active against some viruses. Thus synthesis of such 
derivatives is rather actual.
Two approaches to obtaining analogues of natural nucleosides exist: chemical and 
enzymatic synthesis. 
We investigated the possibility of synthesis of 2-aminobenzimidazole riboside (
3
), 
2’-deoxyriboside (
4
), and 3’-deoxyriboside (
5
) by enzymatic glycosylation using 
nucleoside phosphorylases (
E.coli
PNP and UP) (Scheme 1). Yields of compounds 
3
and 
4
were acceptable but synthesis of 
5
failed (it was shown for the first time). 
According to HPLC data, the conversion of base 
2
to target nucleoside 
5
was less than 
1%
Scheme 1. 
Thus we decided to synthesize nucleoside 
5
from previously obtained riboside 
3
(Scheme 2): 
Scheme 2. 
The chemical synthesis of 3’-deoxyriboside 
5
includes 4 stages. Total yield of the 
target nucleoside - 23%. Purity according to HPLC data - 97%. The structure was 
confirmed by mass- and NMR-spectroscopy. 
The study was supported by RSF grant (Project No. 21-13-00429). 

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Poster presentation 
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