Chiral recognition in the binding of helicenediamine to double strand DNA: interactions between low molecular weight helical compounds and a helical polymer.
Binding of a helicene, 5,8-bis(aminomethyl)-1,12-dimethylbenzo[c]phenanthrene, to calf thymus DNA was studied using UV, CD, and fluorescence spectroscopy as well as calorimetry. The enantiomeric helicenes strongly bound to the double strand DNA possessing the right-handed helical structure. In addition, chiral recognition was observed in the binding, where the (P)-helicene with the right-handed helicity formed more stable complex than the (M)-helicene with the left-handed helicity. The binding studies of the helicenes and natural nucleosides by 1H NMR spectroscopy also revealed the higher affinity to the (P)-helicene. Both monomeric and polymeric nucleic acids thus turned out to favor the (P)-helicity.
Honzawa
Shinobu
S
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai, Japan.
Okubo
Hitoshi
H
Anzai
Shuzo
S
Yamaguchi
Masahiko
M
Tsumoto
Kohei
K
Kumagai
Izumi
I
D002151:Calorimetry; D004247:DNA / Q000378:metabolism*; D008968:Molecular Conformation; D008970:Molecular Weight; D009705:Nucleosides / Q000378:metabolism; D011083:Polycyclic Compounds / Q000737:chemistry / Q000493:pharmacokinetics*; D013057:Spectrum Analysis; D013237:Stereoisomerism; D017186:Titrimetry
D009705:Nucleosides; D011083:Polycyclic Compounds; C475850:helicenediamine; C031660:helicenes; D004247:DNA; C427203:calf thymus DNA