7-Iodo-5-aza-7-deazaguanine ribonucleoside: crystal structure, physical properties, base-pair stability and functionalization

DC FieldValueLanguage
dc.contributor.authorKondhare, Dasharath
dc.contributor.authorBudow-Busse, Simone
dc.contributor.authorDaniliuc, Constantin
dc.contributor.authorSeela, Frank
dc.date.accessioned2021-12-23T16:13:33Z-
dc.date.available2021-12-23T16:13:33Z-
dc.date.issued2020
dc.identifier.issn20532296
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/10627-
dc.description.abstractThe positional change of nitrogen-7 of the RNA constituent guanosine to the bridgehead position-5 leads to the base-modified nucleoside 5-aza-7-deaza-guanosine. Contrary to guanosine, this molecule cannot form Hoogsteen base pairs and the Watson-Crick proton donor site N3-H becomes a proton-acceptor site. This causes changes in nucleobase recognition in nucleic acids and has been used to construct stable `all-purine' DNA and DNA with silver-mediated base pairs. The present work reports the single-crystal X-ray structure of 7-iodo-5-aza-7-deazaguanosine, C10H12IN5O5 (1). The iodinated nucleoside shows an anti conformation at the glycosylic bond and an N conformation (O4'-endo) for the ribose moiety, with an antiperiplanar orientation of the 5'-hydroxy group. Crystal packing is controlled by interactions between nucleobase and sugar moieties. The 7-iodo substituent forms a contact to oxygen-2' of the ribose moiety. Self-pairing of the nucleobases does not take place. A Hirshfeld surface analysis of 1 highlights the contacts of the nucleobase and sugar moiety (O-H center dot center dot center dot O and N-H center dot center dot center dot O). The concept of pK-value differences to evaluate base-pair stability was applied to purine-purine base pairing and stable base pairs were predicted for the construction of `all-purine' RNA. Furthermore, the 7-iodo substituent of 1 was functionalized with benzofuran to detect motional constraints by fluorescence spectroscopy.
dc.description.sponsorshipChemBiotech, Munster, Germany; We thank Dr Peter Leonard for a critical reading of the manuscript. We would like to thank Dr Letzel, OrganischChemisches Institut, Universitat Munster, Germany, for the measurement of the mass spectra and Professor Dr B. Wunsch, Institut fur Pharmazeutische und Medizinische Chemie, Universitat Munster, for providing us with 600 MHz NMR spectra. Funding by ChemBiotech, Munster, Germany, is gratefully acknowledged.
dc.language.isoen
dc.publisherINT UNION CRYSTALLOGRAPHY
dc.relation.ispartofACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
dc.subject5-AZA-7-DEAZA-2'-DEOXYGUANOSINE
dc.subject7-iodo-5-aza-7-deazaguanosine
dc.subjectall-purine RNA
dc.subjectbase-pair prediction
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectCORE
dc.subjectcrystal packing
dc.subjectcrystal structure
dc.subjectCrystallography
dc.subjectDNA
dc.subjectHirshfeld surface analysis
dc.subjectOLIGONUCLEOTIDES
dc.subjectORIENTATION
dc.subjectpK(a) values
dc.subjectribonucleoside
dc.title7-Iodo-5-aza-7-deazaguanine ribonucleoside: crystal structure, physical properties, base-pair stability and functionalization
dc.typejournal article
dc.identifier.doi10.1107/S2053229620004684
dc.identifier.isiISI:000533784500018
dc.description.volume76
dc.description.issue5
dc.description.startpage513+
dc.contributor.orcid0000-0002-6709-3673
dc.contributor.researcheridB-5073-2011
dc.publisher.place2 ABBEY SQ, CHESTER, CH1 2HU, ENGLAND
dcterms.isPartOf.abbreviationActa Crystallogr. Sect. C-Struct. Chem.
dcterms.oaStatusGreen Published, hybrid
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