title: Improved nucleic acid triggered probe activation through the use of a 5-thiomethyluracil peptide nucleic acid building block.
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]
authors.affiliation: Department of Chemistry, Washington University, One Brookings Drive, St. Louis, MO 63130, USA.
authors.forename: Jianfeng
authors.initials: J
authors.lastname: Cai
authors.forename: Xiaoxu
authors.initials: X
authors.lastname: Li
authors.forename: John Stephen
authors.initials: JS
authors.lastname: Taylor
mesh_terms: D001483:Base Sequence; D003374:Coumarins / Q000737:chemistry / Q000493:pharmacokinetics; D004247:DNA / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry / Q000493:pharmacokinetics; D008958:Models, Molecular; D015394:Molecular Structure; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D014498:Uracil / Q000031:analogs & derivatives / Q000737:chemistry* / Q000493:pharmacokinetics
chemical_list: C505900:5-thiomethyluracil; D003374:Coumarins; D007093:Imidazoles; D020135:Peptide Nucleic Acids; D014498:Uracil; D004247:DNA