N7-Guanine as a C+ Mimic in Hairpin aeg/aepPNA-DNA Triplex: Probing Binding Selectivity by UV-Tm and Kinetics by Fluorescence-Based Strand-Invasion Assay
- 1 May 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (11) , 4439-4445
- https://doi.org/10.1021/jo034048h
Abstract
N7-substituted guanine (N7G) has been introduced into aminoethylglycyl bisPNA (7) as a C(+) mimic to achieve pH-independent triplex formation with complementary DNA sequences. The introduction of chiral, cationic aminoethylprolyl units with C(+) and C(+) mimic N7G in the backbone of bisPNAs (8, 9) influenced the recognition of complementary DNA in an orientation-selective manner. A simple fluorescence assay is developed to examine the process of strand invasion of target DNA duplex by these modified bisPNAs and comparative results of the study employing triplex forming polypyrimidine (C/T) (6, 8) and purine-pyrimidine (N7G/T) mixmer-bisPNAs (7, 9) are presented.Keywords
This publication has 17 references indexed in Scilit:
- Aminoethylprolyl (aep) PNA: Mixed Purine/Pyrimidine Oligomers and Binding Orientation Preferences for PNA:DNA Duplex FormationOrganic Letters, 2001
- Peptide Nucleic Acids: Analogs and DerivativesCurrent Organic Chemistry, 2000
- Aminoethylprolyl Peptide Nucleic Acids (aepPNA): Chiral PNA Analogues That Form Highly Stable DNA:aepPNA2 TriplexesOrganic Letters, 1999
- Peptide Nucleic Acid. A Molecule with Two IdentitiesAccounts of Chemical Research, 1999
- Sequence composition effects on the stabilities of triple helix formation by oligonucleotides containing N7-deoxyguanosineNucleic Acids Research, 1996
- Design of an N7-Glycosylated Purine Nucleoside for Recognition of GC Base Pairs by Triple Helix FormationJournal of the American Chemical Society, 1995
- Efficient pH-independent sequence-specific DNA binding by pseudoisocytosine-containing bis-PNANucleic Acids Research, 1995
- Single and Bis Peptide Nucleic Acids as Triplexing Agents: Binding and StoichiometryJournal of the American Chemical Society, 1995
- Intramolecular energy transfer in the inverted regionJournal of the American Chemical Society, 1992
- An in Vivo Model of Somatic Cell Gene Therapy for Human Severe Combined ImmunodeficiencyScience, 1991