title: 7-deaza-2'-deoxyxanthosine: nucleobase protection and base pairing of oligonucleotides.
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.
authors: Laboratorium für Organische und Bioorganische Chemie, Institute für Chemie, Universität Osnabrück, Osnabrück, Germany.
authors: Khalil I
authors: KI
authors: Shaikh
authors: Peter
authors: P
authors: Leonard
authors: Frank
authors: F
authors: Seela
mesh_terms: D020029:Base Pairing; D003853:Deoxyribonucleosides / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D044366:Transition Temperature
chemical_list: C079959:7-deaza-2'-deoxyxanthosine; D003853:Deoxyribonucleosides; D009705:Nucleosides; D009841:Oligonucleotides; D009943:Organophosphorus Compounds