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. 2023 Nov 20;13(11):1676.
doi: 10.3390/biom13111676.

Visible Light-Induced Templated Metathesis of Peptide-Nucleic Acid Conjugates with a Diselenide Bridge

Mateusz Waliczek  1 , Wiktoria Gancarz  1 , Paulina Pochwała  1 , Özge Pehlivan  1 , Piotr Stefanowicz  1
Affiliations

Visible Light-Induced Templated Metathesis of Peptide-Nucleic Acid Conjugates with a Diselenide Bridge

Mateusz Waliczek et al. Biomolecules. .

Abstract

The use of template molecules as chemical scaffolds that significantly influence the course of the reaction has recently been intensively studied. Peptide nucleic acids (PNA) are molecules that mimic natural nucleic acids. They are a promising matrix in such reactions because they possess high affinity and specificity in their interactions. The manner of PNA interaction is predictable based on sequence complementarity. Recently, we report the visible light-induced metathesis reaction in peptides containing a diselenide bond. Herein, we present an efficient and straightforward method of the visible light-driven diselenide-based metathesis of peptide-nucleic acid conjugates. Compared to a similar photochemical transformation in peptides, a significant increase in the metathesis efficiency was obtained due to the template effect.

Keywords: metathesis; peptide nucleic acid; selenium; templated synthesis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Schematic representation of solid-phase assembly of PNA 1.2 conjugates containing diselenide bond.
Figure 2
Figure 2
(A)The structure of N-Fmoc-(Se-Mob-2-selenoethyl)glycine. (B) MS spectrum of the Fmoc-based building block. (C) HPLC chromatogram obtained for Fmoc-based building block and the synthetic pathway for Fmoc derivative.
Figure 3
Figure 3
Schematic representation of diselenide-based visible light-induced metathesis in PNA. (A). parallel direction of hybridization; (B). antiparallel direction of hybridization.
Figure 4
Figure 4
Figure showing the analysis results of PNA 2.1 and 2.2 conjugates after 15 min of irradiation. The structure and MS spectrum of the metathesis product are shown.
Figure 5
Figure 5
HPLC chromatogram obtained for the PNA conjugates 4.1 and 4.2 mixtures containing 2,4-dinitrophenyl chromophore after 60 min of visible light irradiation (at 254 and 365 nm). The bottom figure shows the structure of the metathesis product.
Figure 6
Figure 6
Schematic representation of diselenide-based photoinduced metathesis reaction of PNA conjugates in a three-component system.
See this image and copyright information in PMC

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