Improved nucleic acid triggered probe activation through the use of a 5-thiomethyluracil peptide nucleic acid building block

Org Lett. 2005 Mar 3;7(5):751-4. doi: 10.1021/ol0478382.

Abstract

To improve the efficiency of a nucleic acid triggered probe activation (NATPA) system a 5-thiomethyluracil peptide nucleic acid (PNA) building block has been synthesized. Attachment of imidazole and a coumarin ester to uracils at the ends of two PNAs resulted in a 550 000-fold acceleration of DNA-triggered coumarin release relative to imidazole and a 6-fold increase in k(cat) relative to a system which had these groups attached to the amino and carboxy ends of PNAs. [structure: see text]

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Base Sequence
  • Coumarins / chemistry
  • Coumarins / pharmacokinetics
  • DNA / chemistry*
  • Imidazoles / chemistry
  • Imidazoles / pharmacokinetics
  • Models, Molecular*
  • Molecular Structure
  • Peptide Nucleic Acids / chemical synthesis*
  • Peptide Nucleic Acids / pharmacokinetics
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Uracil / analogs & derivatives
  • Uracil / chemistry*
  • Uracil / pharmacokinetics

Substances

  • 5-thiomethyluracil
  • Coumarins
  • Imidazoles
  • Peptide Nucleic Acids
  • Uracil
  • DNA