Synthesis of a new disulfide Fmoc monomer for creating biologically susceptible linkages in peptide nucleic acid oligomers

Brandon Campbell, Taylor Hood, Nathaniel Shank

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Peptide nucleic acids (PNA) are one of many synthetic mimics of DNA and RNA that have found applications as biological probes, as nano-scaffold components, and in diagnostics. In an effort to use PNA as constructs for cellular delivery we investigated the possibility of installing a biologically susceptible disulfide bond in the backbone of a PNA oligomer. Here we report the synthesis of a new abasic Fmoc monomer containing a disulfide bond that can be incorporated into a PNA oligomer (DS-PNA) using standard solid phase peptide synthesis. The disulfide bond survives cleavage from the resin and DS-PNA forms duplexes with complementary PNA oligomers. Initial studies aimed at determining if the disulfide bond is cleavable to reducing agents while in a duplex are explored using UV thermal analysis and HPLC.

Original languageEnglish
Pages (from-to)394-398
Number of pages5
JournalBioorganic Chemistry
Volume84
DOIs
StatePublished - Mar 2019

Keywords

  • Abasic site
  • Antisense
  • Disulfide cleavage
  • Peptide nucleic acid

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