Submonomeric Strategy with Minimal Protection for the Synthesis of C(2)-Modified Peptide Nucleic Acids

Org Lett. 2021 Feb 5;23(3):902-907. doi: 10.1021/acs.orglett.0c04116. Epub 2021 Jan 8.

Abstract

A novel synthesis of C(2)-modified peptide nucleic acids (PNAs) is proposed, using a submonomeric strategy with minimally protected building blocks, which allowed a reduction in the required synthetic steps. N(3)-unprotected, d-Lys- and d-Arg-based backbones were used to obtain positively charged PNAs with high optical purity, as inferred from chiral GC measurements. "Chiral-box" PNAs targeting the G12D point mutation of the KRAS gene were produced using this method, showing improved sequence selectivity for the mutated- vs wild-type DNA strand with respect to unmodified PNAs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arginine / chemistry*
  • DNA / chemistry*
  • Lysine / chemistry*
  • Molecular Structure
  • Peptide Nucleic Acids / chemical synthesis*
  • Stereoisomerism

Substances

  • Peptide Nucleic Acids
  • DNA
  • Arginine
  • Lysine