2-Azapurine Nucleosides: Synthesis, Properties, and Base Pairing of Oligonucleotides

Autor(en): Budow, Simone
Seela, Frank
Stichwörter: 2-SUBSTITUTED DERIVATIVES; ACYCLIC ANALOGS; ANTIVIRAL ACTIVITY; AZAPURINE NUCLEOSIDES; Biochemistry & Molecular Biology; Chemistry; Chemistry, Multidisciplinary; DNA; FLUORESCENCE PROPERTIES; IMIDAZOLE NUCLEOSIDES; L-HOMOCYSTEINE HYDROLASE; PURINE N-OXIDES; TRICIRIBINE
Erscheinungsdatum: 2010
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMISTRY & BIODIVERSITY
Volumen: 7
Ausgabe: 9
Startseite: 2145
Seitenende: 2190
Zusammenfassung: 
This review deals with 2-azapurine (imidazo[4,5-d][1,2,3]triazine) nucleosides and closely related analogs. Different routes are described to yield the desired target compounds, including a sequence of ring-opening and ring-closure reactions performed on purine nucleosides or direct glycosylation of a 2-azapurine nucleobase with a sugar halide. Further, physical and spectroscopic properties of 2-azapurine nucleosides are discussed, including fluorescence, C-13-NMR data, single-crystal X-ray analyses, and conformation studies on selected compounds; new biological data are presented. The second part of this review is dedicated to oligonucleotides containing 2-azapurines, including building-block (phosphoramidite) preparation and their use in solid-phase oligonucleotide synthesis. Base-pairing properties of 2-azapurine nucleosides as surrogates of canonical constituents of DNA were evaluated.
ISSN: 16121872
DOI: 10.1002/cbdv.201000162

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