Synthesis of Dihydroxyalkynyl and Dihydroxyalkyl Nucleotides as Building Blocks or Precursors for Introduction of Diol or Aldehyde Groups to DNA for Bioconjugations
Language English Country Germany Media print-electronic
Document type Journal Article
- Keywords
- DNA, aldehydes, bioconjugations, reactive groups, reductive amination,
- MeSH
- Adenine analogs & derivatives chemical synthesis chemistry MeSH
- Aldehydes chemistry MeSH
- Amination MeSH
- Cytosine chemistry MeSH
- Deoxyuracil Nucleotides chemical synthesis chemistry MeSH
- DNA-Directed DNA Polymerase chemistry metabolism MeSH
- DNA chemistry metabolism MeSH
- Molecular Structure MeSH
- Nucleotides MeSH
- Uracil chemistry metabolism MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- 7-deazaadenine MeSH Browser
- Adenine MeSH
- Aldehydes MeSH
- Cytosine MeSH
- Deoxyuracil Nucleotides MeSH
- deoxyuridine triphosphate MeSH Browser
- DNA-Directed DNA Polymerase MeSH
- DNA MeSH
- Nucleotides MeSH
- Uracil MeSH
(3,4-Dihydroxybut-1-ynyl)uracil, -cytosine and -7-deazaadenine 2'-deoxyribonucleoside triphosphates (dNTPs) were prepared by direct aqueous Sonogashira cross-coupling of halogenated dNTPs with dihydroxybut-1-yne and converted to 3,4-dihydroxybutyl dNTPs through catalytic hydrogenation. Sodium periodate oxidative cleavage of dihydroxybutyl-dUTP gave the desired aliphatic aldehyde-linked dUTP, whereas the oxidative cleavage of the corresponding deazaadenine dNTP gave a cyclic aminal. All dihydroxyalkyl or -alkynyl dNTPs and the formylethyl-dUTP were good substrates for DNA polymerases and were used for synthesis of diol- or aldehyde-linked DNA. The aldehyde linked DNA was used for the labelling or bioconjugations through hydrazone formation or reductive aminations.
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