Abstract
(Cytosin-5-yl)ethynyl derivatives of pyrimidine and 7-deazaadenine 2-deoxyribonucleosides and nucleoside triphosphates (dNTPs) were prepared in one step by the aqueous Sonogashira coupling of unprotected halogenated nucleos(t)ides with 5-ethynylcytosine. The modified dNTPs were good substrates for DNA polymerases suitable for primer extension or PCR construction of DNA bearing acetylene-linked cytosine(s) in the major groove mimicking the flipped-out nucleotide.
© 2011 American Chemical Society
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetylene / chemistry*
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Adenine / analogs & derivatives
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Adenine / chemical synthesis
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Adenine / chemistry
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Base Sequence
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Cytosine / chemistry*
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DNA / chemistry*
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DNA / genetics
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DNA / metabolism
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DNA-Directed DNA Polymerase / chemistry
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DNA-Directed DNA Polymerase / metabolism*
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Models, Molecular
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Nucleic Acid Conformation*
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Nucleosides / chemical synthesis*
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Nucleosides / chemistry
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Nucleotides / chemical synthesis*
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Nucleotides / chemistry
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Uracil / chemical synthesis
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Uracil / chemistry
Substances
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Nucleosides
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Nucleotides
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7-deazaadenine
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Uracil
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Cytosine
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DNA
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DNA-Directed DNA Polymerase
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Adenine
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Acetylene