Synthesis of biologically active peptide nucleic acid-peptide conjugates by sortase-mediated ligation

J Org Chem. 2007 May 11;72(10):3909-12. doi: 10.1021/jo062331l. Epub 2007 Apr 14.


Sortase A is a transpeptidase that cleaves at a pentapeptide-motif and subsequently transfers the acyl component to a nucleophile containing N-terminal oligoglycines. We investigate the reaction conditions of the sortase-mediated ligation and demonstrate a useful application by the synthesis of a peptide nucleic acid-cell-penetrating peptide chimera, the reaction equilibrium of which can be shifted in favor of the product by dialyzing out the low molecular weight byproduct. The synthesized conjugate exhibits dose-dependent antisense activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Aminoacyltransferases / metabolism*
  • Bacterial Proteins / metabolism*
  • Cysteine Endopeptidases / metabolism*
  • Molecular Sequence Data
  • Nucleic Acids / chemistry*
  • Nucleic Acids / metabolism*
  • Peptides / chemistry*
  • Peptides / metabolism*


  • Bacterial Proteins
  • Nucleic Acids
  • Peptides
  • Aminoacyltransferases
  • sortase A
  • Cysteine Endopeptidases