Silver Ions in Non-canonical DNA Base Pairs: Metal-Mediated Mismatch Stabilization of 2 `-Deoxyadenosine and 7-Deazapurine Derivatives with 2 `-Deoxycytidine and 2 `-Deoxyguanosine

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dc.contributor.authorYang, Haozhe
dc.contributor.authorSeela, Frank
dc.date.accessioned2021-12-23T16:05:41Z-
dc.date.available2021-12-23T16:05:41Z-
dc.date.issued2016
dc.identifier.issn09476539
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7148-
dc.description.abstractNovel silver-mediated dA-dC, dA*-dC, and dA*-dG base pairs were formed in a natural DNA double helix environment (dA* denotes 7-deaza-dA, 7-deaza-7-iodo-dA, and 7-cyclopropyl-7-deaza-dA). 7-Deazapurine nucleosides enforce silver ion binding and direct metal-mediated base pair formation to their Watson-Crick face. New phosphoramidites were prepared from 7-deaza-dA, 7-deaza-7-iodo-dA, and 7-cyclopropyl-7-deaza-dA, which contain labile isobutyryl protecting groups. Solid-phase synthesis furnished oligonucleotides that contain mismatches in near central positions. Increased thermal stabilities (higher T-m values) were observed for oligonucleotide duplexes with non-canonical dA*-dC and dA-dC pairs in the presence of silver ions. The stability of the silver-mediated base pairs was pH dependent. Silver ion binding was not observed for the dA-dG mismatch but took place when mismatches were formed between 7-deazaadenine and guanine. The specific binding of silver ions was confirmed by stoichiometric UV titration experiments, which proved that one silver ion is captured by one mismatch. The stability increase of canonical DNA mismatches might have an impact on cellular DNA repair.
dc.description.sponsorshipChemBiotech, Muster, Germany; China Scholarship Council (CSC), Beijing; Financial support by ChemBiotech, Muster, Germany, and a China Scholarship Council (CSC), Beijing are gratefully acknowledged.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofCHEMISTRY-A EUROPEAN JOURNAL
dc.subjectAB-INITIO
dc.subjectbasepair mismatch
dc.subjectBINDING
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectCRYSTAL-STRUCTURE
dc.subjectCYTOSINE
dc.subjectDNA recognition
dc.subjectdouble-helix stabilization
dc.subjectMAJOR GROOVE
dc.subjectNMR
dc.subjectnucleosides
dc.subjectOLIGONUCLEOTIDE DUPLEXES
dc.subjectPARALLEL
dc.subjectREPAIR
dc.subjectsilver
dc.subjectSTABILITY
dc.titleSilver Ions in Non-canonical DNA Base Pairs: Metal-Mediated Mismatch Stabilization of 2 `-Deoxyadenosine and 7-Deazapurine Derivatives with 2 `-Deoxycytidine and 2 `-Deoxyguanosine
dc.typejournal article
dc.identifier.doi10.1002/chem.201602103
dc.identifier.isiISI:000383763200048
dc.description.volume22
dc.description.issue37
dc.description.startpage13336
dc.description.endpage13346
dc.identifier.eissn15213765
dc.publisher.placePOSTFACH 101161, 69451 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationChem.-Eur. J.
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