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• W3107385089 endingPage "5492" @default.
• W3107385089 startingPage "5492" @default.
• W3107385089 abstract "RNA 5′-modifications are known to extend the functional spectrum of ribonucleotides. In recent years, numerous non-canonical 5′-modifications, including adenosine-containing cofactors from the group of B vitamins, have been confirmed in all kingdoms of life. The structural component of thiamine adenosine triphosphate (thiamine-ATP), a vitamin B1 derivative found to accumulate in Escherichia coli and other organisms in response to metabolic stress conditions, suggests an analogous function as a 5′-modification of RNA. Here, we report the synthesis of thiamine adenosine dinucleotides and the preparation of pure 5′-thiamine-capped RNAs based on phosphorimidazolide chemistry. Furthermore, we present the incorporation of thiamine-ATP and thiamine adenosine diphosphate (thiamine-ADP) as 5′-caps of RNA by T7 RNA polymerase. Transcripts containing the thiamine modification were modified specifically with biotin via a combination of thiazole ring opening, nucleophilic substitution and copper-catalyzed azide-alkyne cycloaddition. The highlighted methods provide easy access to 5′-thiamine RNA, which may be applied in the development of thiamine-specific RNA capture protocols as well as the discovery and confirmation of 5′-thiamine-capped RNAs in various organisms." @default.
• W3107385089 created "2020-12-07" @default.
• W3107385089 creator A5030300808 @default.
• W3107385089 creator A5046855067 @default.
• W3107385089 creator A5057415149 @default.
• W3107385089 date "2020-11-24" @default.
• W3107385089 modified "2023-10-09" @default.
• W3107385089 title "Synthesis of 5′-Thiamine-Capped RNA" @default.
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• W3107385089 doi "https://doi.org/10.3390/molecules25235492" @default.
• W3107385089 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/7727699" @default.
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• W3107385089 hasPublicationYear "2020" @default.
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