Synthesis and DNA binding properties of a new benzo[f]imidazo[1,5b]-isoquinoline-butan-1,2-diol derivative.
A benzo[f]imidazo[1,5b]-isoquinoline derivative 4 with a 1,2-butandiol linker was prepared by reaction of a trimethylsilylated 5-naphthylidenehydantoin 3 with a 2,3-dideoxy-D-glycero-pentafuranoside 2 in 22% yield. After deprotection, the resulting compound 5 was converted to a DMT protected phosphoramidite building block 7 for standard DNA synthesis. DNA/DNA, DNA/RNA duplexes with 5 inserted as bulges were destabilized, except when the new amidite was used for the synthesis of a zipping duplex.
Aly
Youssef L
YL
Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, Odense M, Denmark.
Pedersen
Erik B
EB
D004247:DNA / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D007364:Intercalating Agents / Q000494:pharmacology; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009696:Nucleic Acids / Q000737:chemistry; D009841:Oligonucleotides / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013696:Temperature
D007093:Imidazoles; D007364:Intercalating Agents; D007546:Isoquinolines; D009696:Nucleic Acids; D009841:Oligonucleotides; C516581:benzo(f)imidazo(1,5b)-isoquinoline-butan-1,2-diol; D004247:DNA