Anomeric 2′-Deoxycytidines and Silver Ions: Hybrid Base Pairs with Greatly Enhanced Stability and Efficient DNA Mismatch Detection with α-dC

5 years ago

Anomeric 2′-Deoxycytidines and Silver Ions: Hybrid Base Pairs with Greatly Enhanced Stability and Efficient DNA Mismatch Detection with α-dC

Frank Seela, Xiurong Guo

α-d-Nucleosides are rare in nature but can develop fascinating properties when incorporated into DNA. This work reports on the first silver-mediated base pair constructed from two anomeric nucleosides: α-dC and β-dC. The hybrid base pair was integrated into the DNA and DNA/RNA double helix. A 12-mer duplex with α-dC and β-dC pair exhibits a higher thermal stability (Tm=43 °C) than that incorporating the β-dC–Ag+–β-dC homo pair (Tm=34 °C). Furthermore, α-dC shows excellent mismatch discrimination for DNA single nucleotide polymorphism (SNP). All four SNPs were identified on the basis of large Tm value differences measured in the presence of silver ions. High resolution melting was not required. First anomeric silver connection: A silver-mediated α-dC–β-dC hybrid pair with anomeric cytosine nucleosides was constructed and incorporated into the DNA double helix. It caused greatly enhanced stability over the homo dC–dC pair (see Figure, left) and α-dC shows a high discriminatory power for DNA mismatches identified by large Tm differences in the presence of silver ions (see Figure, right).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201703017