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Homologues of epigenetic pyrimidines: 5-alkyl-, 5-hydroxyalkyl and 5-acyluracil andcytosine nucleotides: synthesis, enzymatic incorporation into DNA and effect on transcription with bacterial RNA polymerase

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F22%3A00559506" target="_blank" >RIV/61388963:_____/22:00559506 - isvavai.cz</a>

  • Alternative codes found

    RIV/61388971:_____/22:00559506 RIV/00216208:11310/22:10454619

  • Result on the web

    <a href="https://doi.org/10.1039/D2CB00133K" target="_blank" >https://doi.org/10.1039/D2CB00133K</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1039/d2cb00133k" target="_blank" >10.1039/d2cb00133k</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Homologues of epigenetic pyrimidines: 5-alkyl-, 5-hydroxyalkyl and 5-acyluracil andcytosine nucleotides: synthesis, enzymatic incorporation into DNA and effect on transcription with bacterial RNA polymerase

  • Original language description

    Homologues of natural epigenetic pyrimidine nucleosides and nucleotides were designed and synthesized. They included 5-ethyl-, 5-propyl-, 5-(1-hydroxyethyl)-, 5-(1-hydroxypropyl)- and 5-acetyl- and 5-propionyl-cytosine anduracil 2'-deoxyribonucleosides and their corresponding 5'-O-triphosphates (dN(x)TPs). The epimers of 5-(1-hydroxyethyl)- and 5-(1-hydroxypropyl)pyrimidine nucleosides were separated and their absolute configuration was determined by a combination of X-ray and NMR analysis. The modified dN(x)TPs were used as substrates for PCR synthesis of modified DNA templates used for the study of transcription with bacterial RNA polymerase. Fundamental differences in transcription efficiency were observed, depending on the various modifications. The most notable effects included pronounced stimulation of transcription from 5-ethyluracil-bearing templates (200% transcription yield compared to natural thymine) and an enhancing effect of 5-acetylcytosine versus inhibiting effect of 5-acetyluracil. In summary, these results reveal that RNA polymerase copes with dramatically altered DNA structure and suggest that these nucleobases could potentially play roles as artificial epigenetic DNA nucleobases.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10608 - Biochemistry and molecular biology

Result continuities

  • Project

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2022

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    RSC Chemical Biology

  • ISSN

    2633-0679

  • e-ISSN

    2633-0679

  • Volume of the periodical

    3

  • Issue of the periodical within the volume

    8

  • Country of publishing house

    GB - UNITED KINGDOM

  • Number of pages

    7

  • Pages from-to

    1069-1075

  • UT code for WoS article

    000825796800001

  • EID of the result in the Scopus database

    2-s2.0-85134389118