2-Allyl- and Propargylamino-dATPs for Site-Specific Enzymatic Introduction of a Single Modification in the Minor Groove of DNA
Language English Country Germany Media print-electronic
Document type Journal Article
Grant support
17-03419S
Grantová Agentura České Republiky
18-03305S
Grantová Agentura České Republiky
CZ.02.1.01/0.0/0.0/16_019/0000729
European Regional Development Fund
H2020-MSCA-ITN-2014-642023
H2020 Marie Skłodowska-Curie Actions
Praemium Academiae
Akademie Věd České Republiky
PubMed
30074286
PubMed Central
PMC6221035
DOI
10.1002/chem.201803973
Knihovny.cz E-resources
- Keywords
- DNA, fluorescent probes, nucleotides, oligonucleotides, polymerases,
- MeSH
- Allyl Compounds chemistry MeSH
- Deoxyadenine Nucleotides chemistry MeSH
- DNA chemistry MeSH
- Fluorescent Dyes chemistry MeSH
- Nucleic Acid Conformation MeSH
- Oligonucleotides analysis MeSH
- Pargyline analogs & derivatives chemistry MeSH
- Propylamines chemistry MeSH
- Fluorescence Resonance Energy Transfer methods MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- 2'-deoxyadenosine triphosphate MeSH Browser
- Allyl Compounds MeSH
- Deoxyadenine Nucleotides MeSH
- DNA MeSH
- Fluorescent Dyes MeSH
- Oligonucleotides MeSH
- Pargyline MeSH
- propargylamine MeSH Browser
- Propylamines MeSH
A series of 2-alkylamino-2'-deoxyadenosine triphosphates (dATP) was prepared and found to be substrates for the Therminator DNA polymerase, which incorporated only one modified nucleotide into the primer. Using a template encoding for two consecutive adenines, conditions were found for incorporation of either one or two modified nucleotides. In all cases, addition of a mixture of natural dNTPs led to primer extension resulting in site-specific single modification of DNA in the minor groove. The allylamino-substituted DNA was used for the thiol-ene addition, whereas the propargylamino-DNA for the CuAAC click reaction was used to label the DNA with a fluorescent dye in the minor groove. The approach was used to construct FRET probes for detection of oligonucleotides.
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