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Updated: Jul 9, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
7-deaza-2'-deoxyxanthosine: nucleobase protection and base pairing of oligonucleotides
Khalil I Shaikh1, Peter Leonard, Frank Seela
1Laboratorium für Organische und Bioorganische Chemie, Institute für Chemie, Universität Osnabrück, Osnabrück, Germany.
Abstract:
Oligonucleotides containing 7-deaza-2'-deoxyxanthosine (1) and 2'-deoxyxanthosine (2) were prepared. The 2-(4-nitrophenyl)ethyl group is applicable for 7-deazaxanthine protection that is removed with DBU by beta-elimination, while the deprotection of the allyl residue with Pd (0) catalyst failed. Contrarily, the allyl group was found to be an excellent protecting group for 2'-deoxyxanthosine (2). The base pairing of nucleosides 1 and 2 with the four canonical DNA constituents as well as with 3 within the 12-mer duplexes is studied.
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