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

DC FieldValueLanguage
dc.contributor.authorBudow, Simone
dc.contributor.authorSeela, Frank
dc.date.accessioned2021-12-23T16:06:40Z-
dc.date.available2021-12-23T16:06:40Z-
dc.date.issued2010
dc.identifier.issn16121872
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7504-
dc.description.abstractThis 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.sponsorshipRoche 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.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofCHEMISTRY & BIODIVERSITY
dc.subject2-SUBSTITUTED DERIVATIVES
dc.subjectACYCLIC ANALOGS
dc.subjectANTIVIRAL ACTIVITY
dc.subjectAZAPURINE NUCLEOSIDES
dc.subjectBiochemistry & Molecular Biology
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDNA
dc.subjectFLUORESCENCE PROPERTIES
dc.subjectIMIDAZOLE NUCLEOSIDES
dc.subjectL-HOMOCYSTEINE HYDROLASE
dc.subjectPURINE N-OXIDES
dc.subjectTRICIRIBINE
dc.title2-Azapurine Nucleosides: Synthesis, Properties, and Base Pairing of Oligonucleotides
dc.typereview
dc.identifier.doi10.1002/cbdv.201000162
dc.identifier.isiISI:000288457500003
dc.description.volume7
dc.description.issue9
dc.description.startpage2145
dc.description.endpage2190
dc.identifier.eissn16121880
dc.publisher.placePOSTFACH 101161, 69451 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationChem. Biodivers.
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