A Facile Synthesis of Red-Shifted Bis-Quinoline (BisQ) Surrogate Base.

ABSTRACT: Forced intercalation peptide nucleic acids (FIT-PNAs) are DNA mimics that act as RNA sensors. The sensing event occurs due to sequence-specific RNA hybridization, leading to a substantial increase in fluorescence. The fluorophore in the FIT-PNA is termed a surrogate base. This molecule typically replaces a purine in the PNA sequence. BisQ is a surrogate base that connects two quinolines via a monomethine bond. BisQ-based FIT-PNAs have excellent biophysical features that include high brightness and red-shifted emission (λ_{em, max} = 613 nm). In this report, we detail two chemical approaches that allow for the facile synthesis of the BisQ PNA monomer. In both cases, the key compound used for the synthesis of BisQ-CH₂COOH is the tBu-ester-modified quinoline synthon (compou

SUBMITTER: Nazzal H 

PROVIDER: S-EPMC11397033 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature