ArticleChemistry (Weinheim an der Bergstrasse, Germany)2026
Halogenated Hypoxanthine 2'-Deoxyribonucleosides With Pyrazolo[3,4-d]Pyrimidine Skeleton: Synthesis, Crystal Structures, Physical Properties, and Impact on Watson-Crick and Purine-Purine Base Pairs.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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Who cites it
1 citing paper in PubMed.
- 7-Deaza-2'-Deoxyxanthosine: Impact of Halogens and Vinyl Side Chains on Purine-Purine Base Pairs in Watson-Crick DNA, Functionalization by Bioorthogonal Inverse-Electron-Demand Diels-Alder Reaction, and Mismatch Discrimination.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
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4 authors.
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Abstract
Syntheses and base pairing properties of halogenated and nonhalogenated hypoxanthine nucleosides with 8-aza-7-deazapurine skeleton (dI*) are reported. Modified hypoxanthine nucleosides were accessed from 6-alkoxy precursors. Single-crystal X-ray analyses disclosed unit cells consisting of two conformers adopting high-anti conformation around the glycosylic bond with N-type C3'-endo (3T2) or E-type, O4'-endo (0E) sugar puckering. Crystal packing is stabilized by inosine/inosine wobble base pairs as well as intermolecular and intramolecular hydrogen bonds. Hirshfeld surface analyses confirmed these findings. Halogenated and nonhalogenated dI* nucleosides were converted to phosphoramidites and applied to solid-phase oligonucleotide synthesis. Single and consecutive incorporations were accomplished and Watson-Crick and purine-purine base pairing was investigated. Single incorporations opposite to canonical nucleosides afforded stable duplexes in all cases. T
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