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Chiral Discrimination of Ofloxacin Enantiomers Using DNA Double Helix Regulated by Metal Ions
Author(s) -
Fu Yan,
Duan Xiaoli,
Chen Xiongfei,
Zhang Haixiang,
Zhang Jinli,
Li Wei
Publication year - 2014
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22287
Subject(s) - chemistry , enantiomer , chirality (physics) , stereoselectivity , dna , desorption , helix (gastropod) , metal , metal ions in aqueous solution , ofloxacin , adsorption , enantiomeric excess , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , biochemistry , ecology , antibiotics , ciprofloxacin , snail , biology , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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. Chirality 26:249–254, 2014 . © 2014 Wiley Periodicals, Inc.