Chiral discrimination of ofloxacin enantiomers using DNA double helix regulated by metal ions.
DNA-based chiral selectors are constructed to discriminate ofloxacin enantiomers through metal-ion anchoring on a special DNA double helix that contains successive GC pairs. The effects of metal ions involving Mg(2+), Ni(2+), Cu(2+), Ag(+), and Pt(2+) were studied on the regulation of DNA chiral discrimination towards ofloxacin enantiomers. It is shown that DNA-Cu(II) complexes exhibit the highest enantioselectivities at the [Cu(2+)]/base ratio of 0.1. The enantiomeric excess can reach 59% in R-enantiomer after being adsorbed by the RET-Cu(II) complex. Stereoselective recognition of ofloxacin enantiomers on the double helix is tunable via external stimulus, providing a programmable desorption process to regenerate DNA. This DNA-based chiral selector exhibits excellent reusability without apparent loss of enantioselectivity after three cycles of adsorption and desorption.
Key Laboratory of Systems Bioengineering MOE, Key Laboratory for Green Chemical Technology MOE, Tianjin University, Tianjin, People's Republic of China.
Yan
Y
Fu
Xiaoli
X
Duan
Xiongfei
X
Chen
Haixiang
H
Zhang
Jinli
J
Zhang
Wei
W
Li
D004247:DNA / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D015242:Ofloxacin / Q000737:chemistry* / Q000302:isolation & purification*; D013237:Stereoisomerism; D013379:Substrate Specificity; D028561:Transition Elements / Q000737:chemistry*
D008670:Metals; D028561:Transition Elements; D004247:DNA; D015242:Ofloxacin
DNA; assembly; biomacromolecule; chiral drug; chirality; enantioselectivity; metal ion; molecular recognition; stereoselectivity; stimuli