2-Azapurine Nucleosides: Synthesis, Properties, and Base Pairing of Oligonucleotides
DC Element | Wert | Sprache |
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dc.contributor.author | Budow, Simone | |
dc.contributor.author | Seela, Frank | |
dc.date.accessioned | 2021-12-23T16:06:40Z | - |
dc.date.available | 2021-12-23T16:06:40Z | - |
dc.date.issued | 2010 | |
dc.identifier.issn | 16121872 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/7504 | - |
dc.description.abstract | 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. | |
dc.description.sponsorship | Roche Diagnostics GmbH; ChemBiotech, Munster, Germany; We thank Prof. Dr. Igor A. Mikhailopulo for the PSEUROT calculations of some compounds. We acknowledge Prof. Dr. Gilles Gosselin for the evaluation of the antiviral data. We are grateful for critical reading of the manuscript by Dr. Peter Leonard and Mr. Suresh S. Pujari. Financial support by the Roche Diagnostics GmbH and ChemBiotech, Munster, Germany, is gratefully acknowledged. | |
dc.language.iso | en | |
dc.publisher | WILEY-V C H VERLAG GMBH | |
dc.relation.ispartof | CHEMISTRY & BIODIVERSITY | |
dc.subject | 2-SUBSTITUTED DERIVATIVES | |
dc.subject | ACYCLIC ANALOGS | |
dc.subject | ANTIVIRAL ACTIVITY | |
dc.subject | AZAPURINE NUCLEOSIDES | |
dc.subject | Biochemistry & Molecular Biology | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | DNA | |
dc.subject | FLUORESCENCE PROPERTIES | |
dc.subject | IMIDAZOLE NUCLEOSIDES | |
dc.subject | L-HOMOCYSTEINE HYDROLASE | |
dc.subject | PURINE N-OXIDES | |
dc.subject | TRICIRIBINE | |
dc.title | 2-Azapurine Nucleosides: Synthesis, Properties, and Base Pairing of Oligonucleotides | |
dc.type | review | |
dc.identifier.doi | 10.1002/cbdv.201000162 | |
dc.identifier.isi | ISI:000288457500003 | |
dc.description.volume | 7 | |
dc.description.issue | 9 | |
dc.description.startpage | 2145 | |
dc.description.endpage | 2190 | |
dc.identifier.eissn | 16121880 | |
dc.publisher.place | POSTFACH 101161, 69451 WEINHEIM, GERMANY | |
dcterms.isPartOf.abbreviation | Chem. Biodivers. |
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geprüft am 17.05.2024