Highly efficient strand invasion by peptide nucleic acid bearing optically pure lysine residues in its backbone

Nucleic Acids Symp Ser (Oxf). 2006:(50):109-10. doi: 10.1093/nass/nrl054.

Abstract

Chiral PNA monomers (PNA = peptide nucleic acid), in which nucleobases are attached to N-(aminoethyl)-D-lysine, were introduced to PNAs bearing pseudo-complementary nucleobases (2,6-diaminopurine and 2-thiouracil). When these highly cationic PNAs targeted double-stranded DNA, they invaded there much more efficiently than conventional pseudo-complementary PNAs composed of achiral PNA monomers. Although introduction of N-(aminoethyl)-D-lysine backbone was effective for promotion of strand invasion, L-isomer never promote it. Simple incorporation of lysine groups to the termini of PNA was also ineffective, indicating that introduction of positive charges into PNA backbone is important. Even highly G-C rich sequence, which conventional pseudo-complementary PNAs never invade, was successfully targeted based on this strategy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Aminopurine / analogs & derivatives
  • 2-Aminopurine / chemistry
  • DNA / chemistry*
  • Electrophoretic Mobility Shift Assay
  • GC Rich Sequence
  • Isomerism
  • Lysine / analogs & derivatives*
  • Lysine / chemistry
  • Peptide Nucleic Acids / chemistry*
  • Static Electricity
  • Thiouracil / chemistry

Substances

  • Peptide Nucleic Acids
  • 2-Aminopurine
  • 2,6-diaminopurine
  • Thiouracil
  • DNA
  • Lysine