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Bacteriophage-related epigenetic natural and non-natural pyrimidine nucleotides and their influence on transcription with T7 RNA polymerase
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SYSNO ASEP 0600677 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Bacteriophage-related epigenetic natural and non-natural pyrimidine nucleotides and their influence on transcription with T7 RNA polymerase Author(s) Gracias, Filip (UOCHB-X) ORCID
Pohl, Radek (UOCHB-X) RID, ORCID
Sýkorová, Veronika (UOCHB-X) ORCID, RID
Hocek, Michal (UOCHB-X) RID, ORCIDArticle number 256 Source Title Communications Chemistry. - : Nature Publishing Group - ISSN 2399-3669
Roč. 7, November (2024)Number of pages 11 s. Language eng - English Country US - United States Keywords major groove ; deoxyribonucleic acid ; modified base OECD category Biochemistry and molecular biology R&D Projects EH22_008/0004575 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UOCHB-X - RVO:61388963 UT WOS 001351596800002 EID SCOPUS 85209818120 DOI https://doi.org/10.1038/s42004-024-01354-5 Annotation DNA modifications on pyrimidine nucleobases play diverse roles in biology such as protection of bacteriophage DNA from enzymatic cleavage, however, their role in the regulation of transcription is underexplored. We have designed and synthesized a series of uracil 2ʹ-deoxyribonucleosides and 5ʹ-O-triphosphates (dNTPs) bearing diverse modifications at position 5 of nucleobase, including natural nucleotides occurring in bacteriophages, α-putrescinylthymine, α-glutaminylthymine, 5-dihydroxypentyluracil, and methylated or non-methylated 5-aminomethyluracil, and non-natural 5-sulfanylmethyl- and 5-cyanomethyluracil. The dNTPs bearing basic substituents were moderate to poor substrates for DNA polymerases, but still useful in primer extension synthesis of modified DNA. Together with previously reported epigenetic pyrimidine nucleotides, they were used for the synthesis of diverse DNA templates containing a T7 promoter modified in the sense, antisense or in both strands. A systematic study of the in vitro transcription with T7 RNA polymerase showed a moderate positive effect of most of the uracil modifications in the non-template strand and some either positive or negative influence of modifications in the template strand. The most interesting modification was the non-natural 5-cyanomethyluracil which showed significant positive effect in transcription. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2025 Electronic address https://doi.org/10.1038/s42004-024-01354-5
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