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- Title
Rapid Synthesis of Propargyl‐γ‐Modified Peptide Nucleic Acid Monomers for Late‐Stage Functionalization of Oligomers.
- Authors
López‐Tena, Miguel; Watson, Emma E.; Romanens, Patrick; Winssinger, Nicolas
- Abstract
The exceptional hybridization properties of peptide nucleic acids (PNAs) coupled with the ease of their synthesis has made this artificial nucleic acid mimetic a desirable platform for diagnostics, therapeutics and supramolecular engineering. PNA backbone modifications have been extensively explored to finetune physicochemical properties and for conjugation of functional molecules. Here, we detail the synthesis of a universal γ‐propargyl‐PNA backbone from serine, and its acylation with the four DNA canonical nucleobases. The availability of serine as d or l enantiomer provide simple accesses to PNA oligomers for hybridization with natural oligonucleotides or for orthogonal hybridization circuitry. We show that late‐stage conjugation enables optimization of the physicochemical properties. This approach is appealing due to its orthogonality to Fmoc‐SPPS, its flexibility and ease for introducing diversity by on‐resin copper(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC). We exemplified the utility of these novel monomers with PNA based hybridization chain reactions (HCRs).
- Subjects
PEPTIDE nucleic acids; PEPTIDE synthesis; MONOMERS; OLIGOMERS; NUCLEIC acids; OLIGONUCLEOTIDES; COPPER
- Publication
Helvetica Chimica Acta, 2023, Vol 106, Issue 11, p1
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.202300110