Silver-Mediated Base Pairs in DNA Incorporating Purines, 7-Deazapurines, and 8-Aza-7-deazapurines: Impact of Reduced Nucleobase Binding Sites and an Altered Glycosylation Position

Autor(en): Zhao, Hang
Leonard, Peter
Guo, Xiurong
Yang, Haozhe
Seela, Frank
Stichwörter: base pairs; Chemistry; Chemistry, Multidisciplinary; COMPLEXES; DEOXYRIBONUCLEIC-ACID; DERIVATIVES; DNA; duplex stability; METAL-IONS; NMR; nucleic acids; NUCLEIC-ACIDS; NUCLEOSIDES; OLIGONUCLEOTIDE DUPLEXES; PARALLEL; silver ions; STABILITY
Erscheinungsdatum: 2017
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMISTRY-A EUROPEAN JOURNAL
Volumen: 23
Ausgabe: 23
Startseite: 5529
Seitenende: 5540
Zusammenfassung: 
Formation of silver-mediated DNA was studied with oligonucleotides incorporating 8-aza-7-deazapurine, 7-deazapurine, and purine nucleosides. The investigation was performed on non-self-complementary duplexes with one or two modifications and self-complementary duplexes with an alternating dA-dT motif. Homo base pairs as well as base pair mismatches of dA analogues with dC and Watson-Crick pairs with dT were studied by stoichiometric silver ion titration and T-m measurements. N-8-Glycosylated 8-aza-7-deazaadenine forms silver-ion-mediated base pairs capturing two silver ions (low silver content) whereas regularly glycosylated 8-aza-7-deazapurine, 7-deazapurine (c(7)A(d)), and dA do not form comparable structures. Stable silver-mediated dA-dC base pair mismatches were detected for all nucleosides. Two silver ions per base pair are bound by 8-aza-7-deazapurine whereas c(7)A(d) binds only one silver ion. The situation is different when the equivalents of silver ions were increased to the number of total base pairs. Surprisingly, in 12-mer duplexes as well as in related 25-mer duplexes every base pair consumed one silver ion.
ISSN: 09476539
DOI: 10.1002/chem.201605982

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