Design of triple helix forming C-glycoside molecules.
The modeling, synthesis, and characterization of oligomers containing 2-aminoquinazolin-5-yl 2'-deoxynucleotide residues are reported. The 2-aminoquinazoline residues sequence specifically bind via Hoogsteen base pairing as a third strand in the center of the major groove at T:A base pair Watson-Crick duplex sequences. Evidence for the formation of a sequence specific three-stranded structure is based on thermal denaturation UV-vis and fluorescence studies. The novel 2-aminoquinazoline C-nucleotide is a component of a system designed to overcome the homopurine requirement for triple helix structures.
Li
Jian-Sen
JS
Eppley Institute for Research in Cancer, Department of Pharmaceutical Sciences, University of Nebraska Medical Center, 986805 Nebraska Medical Center, Omaha, Nebraska 68198-6805, USA.
Fan
Yun-Hua
YH
Zhang
Yi
Y
Marky
Luis A
LA
Gold
Barry
B
D002942:Circular Dichroism; D004247:DNA / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D011799:Quinazolines / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
D006027:Glycosides; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D011799:Quinazolines; C434331:phosphoramidite; C051802:triplex DNA; D004247:DNA