A new approach to the synthesis of Anti-Reverse Cap Analog (ARCA) 2mGpppG
- Authors: Kayushin A.L.1, Antonov K.V.1, Dorofeeva E.V.1, Berzina M.Y.1, Arnautova A.O.1, Prohorenko I.A.1, Miroshnikov A.I.1, Konstantinova I.D.1
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Affiliations:
- Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
- Issue: Vol 50, No 1 (2024)
- Pages: 3-10
- Section: Articles
- URL: https://journals.rcsi.science/0132-3423/article/view/258137
- DOI: https://doi.org/10.31857/S0132342324010015
- EDN: https://elibrary.ru/QSYRGR
- ID: 258137
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Abstract
A new approach to the synthesis of Anti-Reverse Cap Analog (ARCA) of the classical structure – dimethylated guanosine dinucleotide 2mGpppG is proposed. The classical approach to obtaining consists in condensation of activated 5′-diphosphate of 7,3′-O-dimethylguanosine with 5′-guanosine monophosphate. We suggest to use a commercially available 3′-O-methylguanosine for the synthesis of 5′-monophosphate of dimethylated guanosine only, and to use an activated 5′-guanosine diphosphate in the condensation. The conditions of 3′-O-methylguanosine phosphorylation were determined to avoid the formation of a side product 3′-O-methyl-5′-deoxy-5′-chloroguanosine-3′-phosphate. ARCA was synthesized with a high yield (89% at the condensation stage). Our approach to the synthesis is easily scaled and can be used for a preparative synthesis of ARCA (several grams).
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About the authors
A. L. Kayushin
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Author for correspondence.
Email: kayushin.alexej@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
K. V. Antonov
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
E. V. Dorofeeva
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
M. Y. Berzina
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
A. O. Arnautova
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
I. A. Prohorenko
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
A. I. Miroshnikov
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
I. D. Konstantinova
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
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