Journal article

Improved synthesis of phosphoramidite-protected N6-methyladenosine via BOP-mediated SNAr reaction

Abstract:: N⁶-methyladenosine(m⁶A) is the most abundant modification in mRNA. Studies on proteins that introduce and bind m⁶A require the efficient synthesis of oligonucleotides containing m⁶A. We report an improved five-step synthesis of the m⁶A phosphoramidite starting from inosine, utilising a 1-H-benzotriazol-1-yloxytris(dimethylamino)phosphoniumhexafluorophosphate (BOP)_-mediated S_NAr reaction in the key step. The route manifests a substantial increase in overall yield compared to reported routes, and is useful for the synthesis of phosphoramidites of other adenosine derivatives, such as ethanoadenosine, an RNA analogue of the DNA adduct formed by the important anticancer drug Carmustine.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Shishodia, S., & Schofield, C. J. (2020). Improved synthesis of phosphoramidite-protected N6-methyladenosine via BOP-mediated SNAr reaction. Molecules, 26(1).

MLA Style

Shishodia, S., and C. J. Schofield. “Improved Synthesis of Phosphoramidite-Protected N6-Methyladenosine via BOP-Mediated SNAr Reaction.” Molecules, vol. 26, no. 1, MDPI, 2020.

Chicago Style

Shishodia, S, and CJ Schofield. 2020. “Improved Synthesis of Phosphoramidite-Protected N6-Methyladenosine via BOP-Mediated SNAr Reaction.” Molecules 26 (1).
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Files:: Shishodia_and_Schofield_2021_improved_synthesis_of.pdf

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Publisher copy:: 10.3390/molecules26010147

Authors

+ Shishodia, S More by this author

Role:: Author

+ Schofield, CJ More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author
ORCID:: 0000-0002-0290-6565

+ Wellcome Trust More from this funder

Publisher:: MDPI
Journal:: Molecules More from this journal
Volume:: 26
Issue:: 1
Article number:: 147
Place of publication:: Switzerland
Publication date:: 2020-12-31
Acceptance date:: 2020-12-18
DOI:: 10.3390/molecules26010147
EISSN:: 1420-3049
Pmid:: 33396208

Language:: English
Keywords:: adenosine

DNA adducts

FFR

organophosphorus compounds

catalysis
Pubs id:: 1151566
Local pid:: pubs:1151566
Deposit date:: 2021-09-16

Terms of use

Copyright holder:: Shishodia and Schofield
Copyright date:: 2020
Rights statement:: © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/).

Licence:: CC Attribution (CC BY)

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