Enviar artigo por via de e-mail A new approach to the synthesis of Anti-Reverse Cap Analog (ARCA) 2mGpppG
- Autores: 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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Afiliações:
- Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
- Edição: Volume 50, Nº 1 (2024)
- Páginas: 3-10
- Seção: Articles
- URL: https://cijournal.ru/0132-3423/article/view/670982
- DOI: https://doi.org/10.31857/S0132342324010015
- EDN: https://elibrary.ru/QSYRGR
- ID: 670982
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Resumo
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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Sobre autores
A. Kayushin
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Autor responsável pela correspondência
Email: kayushin.alexej@yandex.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997
K. Antonov
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997
E. Dorofeeva
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997
M. Berzina
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997
A. Arnautova
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997
I. Prohorenko
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997
A. Miroshnikov
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997
I. Konstantinova
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: kayushin.alexej@yandex.ru
Rússia, ul. Miklukho-Maklaya 16/10, Moscow, 117997
Bibliografia
- Peng Z.-H., Sharma V., Scott F. Singleton S.F., Paul D. Gershon P.D. // Org. Lett. 2002. V. 4. P. 161–164. https://doi.org/10.1021/ol0167715
- Rydzik A.M., Lukaszewicz M., Zuberek J., Kowalska J., Darzynkiewicz Z.M., Darzynkiewicz E., Jemielity J. // Org. Biomol. Chem. 2009. V. 7. P. 4763–4776. https://doi.org/10.1039/B911347A
- Grudzien-Nogalska E., Stepinski J., Jemielity J., Zuberek J., Stolarski R., Rhoads R.E, Darzynkiewicz E. // Methods Enzymol. 2007. V. 431. P. 203–227. https://doi.org/10.1016/S0076-6879(07)31011-2
- Stepinski J., Waddell C., Stolarski R., Darzynkiewicz E., Rhoads R.E. // RNA. 2001. V. 7. P. 1486–1495.
- Jemielity J., Fowler T., Zuberek J., Stepinski J., Lewdorowicz M., Niedzwiecka A., Stolarski R., Darzynkiewicz E., Rhoads R.E. // RNA. 2003. V. 9. P. 1108–1122. https://doi.org/10.1261/rna.5430403
- Yoshikawa М., Kato T., Takenishi T. // Bull. Chem. Soc. Jap. 1969. V. 42. P. 3505–3508.
- Kadokura M., Wada T., Urashima C., Sekine M. // Tetrahedron Lett. 1997. V. 38. P. 8359–8362. https://doi.org/10.1016/S0040-4039(97)10263-5
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