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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geprüft am 03.05.2024