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 DOI Creative Commons
A. Hasan Howlader, Raúl Fernández, Pawlos S. Tsegay

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(6), P. 1358 - 1358

Published: March 18, 2025

Iodosulfonylation of an ethynyl group at the C2 position 2′-deoxyadenosine or adenosine with TsI provides (E)-2-(β-iodovinyl)sulfones. The latter undergo nucleophilic substitution amines via addition–elimination to give β-sulfonylvinylamines (enamines). Acid-catalyzed hydrolysis 2-(β-keto)sulfones, mechanistically different probes that react alkyl halides, resulting in α-alkylation. Adenine nucleosides a β-ketosulfone C2, during conversion their 5′-triphosphate form, unexpected 2-carboxylic acid nucleotides. 2′-deoxyadenosine-2-carboxylic was incorporated by human DNA polymerase into one-nucleotide gap substrate.

Language: Английский

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 DOI Creative Commons
A. Hasan Howlader, Raúl Fernández, Pawlos S. Tsegay

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(6), P. 1358 - 1358

Published: March 18, 2025

Iodosulfonylation of an ethynyl group at the C2 position 2′-deoxyadenosine or adenosine with TsI provides (E)-2-(β-iodovinyl)sulfones. The latter undergo nucleophilic substitution amines via addition–elimination to give β-sulfonylvinylamines (enamines). Acid-catalyzed hydrolysis 2-(β-keto)sulfones, mechanistically different probes that react alkyl halides, resulting in α-alkylation. Adenine nucleosides a β-ketosulfone C2, during conversion their 5′-triphosphate form, unexpected 2-carboxylic acid nucleotides. 2′-deoxyadenosine-2-carboxylic was incorporated by human DNA polymerase into one-nucleotide gap substrate.

Language: Английский

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