title: Nucleobase-caged peptide nucleic acids: PNA/PNA duplex destabilization and light-triggered PNA/PNA recognition.
abstract: The 2-(o-nitrophenyl)-propyl (NPP) group is used as caging group to mask the nucleobases adenine and cytosine in N-(2-aminoethyl)glycine peptide nucleic acids (aeg-PNA). The adeninyl and cytosinyl nucleo amino acid building blocks Fmoc-a(NPP) -aeg-OH and Fmoc-c(NPP) -aeg-OH were synthesized and incorporated into PNA sequences by Fmoc solid phase synthesis relying on high stability of the NPP nucleobase protecting group toward Fmoc-cleavage, coupling, capping, and resin cleavage conditions. Removal of the nucleobase caging group was achieved by UV-LED irradiation at 365 nm. The nucleobase caging groups provided sterical crowding effecting the Watson-Crick base pairing, and thereby, the PNA double strand stabilities. Duplex formation can completely be suppressed for complementary PNA containing caging groups in both strands. PNA/PNA recognition can be completely restored by UV light-triggered release of the photolabile protecting group.
authors: Institut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany.
authors: Samit
authors: S
authors: Guha
authors: Julia
authors: J
authors: Graf
authors: Björn
authors: B
authors: Göricke
authors: Ulf
authors: U
authors: Diederichsen
mesh_terms: D008027:Light; D015394:Molecular Structure; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D013696:Temperature; D014466:Ultraviolet Rays
chemical_list: D020135:Peptide Nucleic Acids