Synthesis, incorporation into triplex-forming oligonucleotide, and binding properties of a novel 2'-deoxy-C-nucleoside featuring a 6-(thiazolyl-5)benzimidazole nucleobase.
[reaction: see text] 6-(Thiazolyl-5)benzimidazole (B(t)()) was designed as a novel nucleobase for the specific recognition of an inverted A.T base pair in a triple helix motif. It was successfully incorporated into an 18-mer triplex-forming oligonucleotide (TFO) using the 2'-deoxy-C-nucleoside phosphoramidite 16. The triple helix binding properties of the modified TFO were examined by means of thermal denaturation experiments targeting an oligopyrimidine.oligopurine 26-mer DNA duplex containing an A.T base pair inversion.
Guianvarc'h
Dominique
D
Institut de Chimie des Substances Naturelles, CNRS, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Fourrey
Jean-Louis
JL
Maurisse
Rosalie
R
Sun
Jian-Sheng
JS
Benhida
Rachid
R
D000225:Adenine / Q000737:chemistry; D001483:Base Sequence; D001562:Benzimidazoles / Q000737:chemistry*; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009691:Nucleic Acid Denaturation; D009705:Nucleosides / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D013696:Temperature; D013941:Thymine / Q000737:chemistry
C470640:6-(thiazolyl-5)benzimidazole; D001562:Benzimidazoles; D009705:Nucleosides; D009841:Oligonucleotides; C051802:triplex DNA; D004247:DNA; D000225:Adenine; D013941:Thymine