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- Title
Mirror‐Image Dependence: Targeting Enantiomeric G‐Quadruplex DNA Using Triplex Metallohelices.
- Authors
Zhao, Chuanqi; Song, Hualong; Scott, Peter; Zhao, Andong; Tateishi‐Karimata, Hisae; Sugimoto, Naoki; Ren, Jinsong; Qu, Xiaogang
- Abstract
Natural d‐DNA and l‐DNA are mirror‐image counterparts. However, because of the inherent flexibility and conformation diversity of DNA, it is still not clear how enantiomeric compounds recognize d‐DNA and l‐DNA. Herein, taking G‐quadruplex (G4) DNA as an example that has diverse conformations and distinct biofunctions, the binding of ten pairs of iron triplex metallohelices to d‐ and l‐G4 DNA were evaluated. The Δ‐enantiomer binds to d‐DNA and the Λ‐enantiomer binds to l‐DNA, exhibiting almost the same stabilization effect and binding affinity. The binding affinity of the Δ‐metallohelix with d‐G4 is nearly 70‐fold higher than that of Λ‐metallohelix binding d‐G4. Δ‐Metallohelix binding to d‐G4 follows a two‐step binding process driven by a favorable enthalpy contribution to compensate for the associated unfavorable entropy.
- Subjects
OLIGONUCLEOTIDES; DNA; NUCLEIC acids; ENTHALPY; BASE pairs
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 48, p15949
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201809207