1. A Bifunctional Monomer for On-Resin Synthesis of Polyfunctional PNAs and Tailored Induced-Fit Switching Probes
- Author
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Manicardi, Alex, Bertucci, Alessandro, Rozzi, Andrea, and Corradini, Roberto
- Subjects
Peptide nucleic acid ,010405 organic chemistry ,Oligonucleotide ,Stereochemistry ,Organic Chemistry ,Substituent ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Combinatorial chemistry ,0104 chemical sciences ,Nucleobase ,chemistry.chemical_compound ,Monomer ,chemistry ,Molecular beacon ,Pyrene ,Physical and Theoretical Chemistry ,Bifunctional - Abstract
A synthetic strategy for the production of polyfunctional PNAs bearing substituent groups both on the nucleobase and on the backbone C5 carbon of the same monomer is described; this is based on the use of a tris-orthogonally protected monomer and subsequent solid-phase selective functionalization. This strategy can be used for synthesizing PNAs that are not readily accessible by use of preformed modified monomers. As an example, a PNA-based probe that undergoes a switch in its fluorescence emission upon hybridization with a target oligonucleotide, induced by tailor-made movement of two pyrene substituent groups, was synthesized.
- Published
- 2016