Silver-Mediated Homochiral and Heterochiral alpha-dC/beta-dC Base Pairs: Synthesis of alpha-dC through Glycosylation and Impact of Consecutive, Isolated, and Multiple Metal Ion Pairs on DNA Stability

Autor(en): Chai, Yingying
Leonard, Peter
Guo, Xiurong
Seela, Frank
Stichwörter: ANALOGS; base pairing; BINDING; Chemistry; Chemistry, Multidisciplinary; circular dichroism; COMPONENTS; DEOXYRIBONUCLEIC-ACID; DERIVATIVES; DNA; DUPLEX; ENHANCED STABILITY; NUCLEIC-ACIDS; nucleobases; NUCLEOSIDES; PARALLEL; silver
Erscheinungsdatum: 2019
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMISTRY-A EUROPEAN JOURNAL
Volumen: 25
Ausgabe: 72
Startseite: 16639
Seitenende: 16651
Zusammenfassung: 
Isolated and consecutive heterochiral alpha-dC- base pairs have been incorporated into 12-mer oligonucleotide duplexes at various positions, thereby replacing Watson-Crick pairs. To this end, a new synthesis of the alpha-d anomer of dC has been developed, and oligonucleotides containing alpha-dC residues have been synthesized. Silver-mediated base pairs were formed upon the addition of silver ions. Furthermore, we have established that heterochiral alpha-dC-dC base pairs can approach the stability of a Watson-Crick pair, whereas homochiral dC-dC pairs are significantly less stable. A positional change of the silver-mediated base pairs affects the duplex stability and reveals the nearest-neighbor influence. When the number of silver ions was equivalent to the number of duplex base pairs (12), non-melting silver-rich complexes were formed. Structural changes have been supported by circular dichroism (CD) spectra, which showed that the B-DNA structure was maintained whilst the silver ion concentration was low. At high silver ion concentration, silver-rich complexes displaying different CD spectra were formed.
ISSN: 09476539
DOI: 10.1002/chem.201903915

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