Synthesis of Adenine Nucleosides with a Reactive (β-Iodovinyl)sulfone or (β-Keto)sulfone Group at the C2 Position and Their Polymerase-Catalyzed Incorporation into DNA
2025
A. Hasan Howlader | Richard Fernandez | Pawlos S. Tsegay | Yuan Liu | Stanislaw F. Wnuk
Iodosulfonylation of an ethynyl group at the C2 position of 2&prime:-deoxyadenosine or adenosine with TsI provides (E)-2-(&beta:-iodovinyl)sulfones. The latter undergo nucleophilic substitution with amines via an addition&ndash:elimination to give &beta:-sulfonylvinylamines (enamines). Acid-catalyzed hydrolysis of the &beta:-sulfonylvinylamines provides 2-(&beta:-keto)sulfones, mechanistically different probes that react with alkyl halides, resulting in &alpha:-alkylation. Adenine nucleosides with a &beta:-ketosulfone group at C2, during conversion to their 5&prime:-triphosphate form, undergo an unexpected conversion to 2-carboxylic acid nucleotides. The 5&prime:-triphosphate of 2&prime:-deoxyadenosine-2-carboxylic acid was incorporated by a human DNA polymerase into a one-nucleotide gap DNA substrate.
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